KEMPER STRATEGIC INCOME FUND
N-30D, 2000-07-25
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<PAGE>   1

LONG-TERM INVESTING IN A SHORT-TERM WORLD(SM)

                                                            SEMIANNUAL REPORT TO
                                                     SHAREHOLDERS FOR THE PERIOD
                                                              ENDED MAY 31, 2000

KEMPER STRATEGIC
INCOME TRUST

        "... Emerging-market bonds were the trust's bright spot, as returns from
                                       domestic high-yield bonds were weak. ..."

                                                             [KEMPER FUNDS LOGO]
<PAGE>   2

CONTENTS
3
ECONOMIC OVERVIEW
5
MANAGEMENT TEAM
6
PERFORMANCE UPDATE
8
PORTFOLIO STATISTICS
9
PORTFOLIO OF
INVESTMENTS
13
FINANCIAL STATEMENTS
17
FINANCIAL HIGHLIGHTS
18
NOTES TO
FINANCIAL STATEMENTS
21

SHAREHOLDERS' MEETING

AT A GLANCE

 KEMPER STRATEGIC INCOME TRUST
 TOTAL RETURNS
 FOR THE SIX-MONTH PERIOD ENDED MAY 31, 2000

<TABLE>
<S> <C>                                        <C>   <C>
 ........................................................
    BASED ON NET ASSET VALUE                   2.06%
 ........................................................
    BASED ON MARKET PRICE                      5.09%
 ........................................................
</TABLE>

 NET ASSET VALUE AND MARKET PRICE

<TABLE>
<CAPTION>
                                   AS OF     AS OF
                                  5/31/00   11/30/99
 ........................................................
<S> <C>                           <C>       <C>      <C>
    NET ASSET VALUE                $12.29     $12.88
 ........................................................
    MARKET PRICE                   $13.94     $14.19
 ........................................................
</TABLE>

THE TRUST MAY INVEST IN LOWER-RATED AND NONRATED SECURITIES, WHICH PRESENT
GREATER RISK OF LOSS TO PRINCIPAL AND INTEREST THAN HIGHER-RATED SECURITIES, AND
IN FOREIGN SECURITIES, WHICH PRESENT SPECIAL RISK CONSIDERATIONS INCLUDING
FLUCTUATING FOREIGN EXCHANGE RATES, FOREIGN GOVERNMENT REGULATIONS AND DIFFERING
DEGREES OF LIQUIDITY.


DIVIDEND REVIEW

THE FOLLOWING TABLE SHOWS PER SHARE DIVIDEND AND YIELD INFORMATION FOR THE
TRUST AS OF MAY 31, 2000.

<TABLE>
<CAPTION>
                                      KEMPER STRATEGIC
                                        INCOME TRUST
 ............................................................
<S> <C>                             <C>                  <C>
    SIX-MONTHS INCOME                      $0.90
 ............................................................
    MAY DIVIDEND                           $0.15
 ............................................................
    ANNUALIZED DISTRIBUTION RATE
    (BASED ON NET ASSET VALUE)             14.64%
 ............................................................
    ANNUALIZED DISTRIBUTION RATE
    (BASED ON MARKET VALUE)                12.91%
 ............................................................
</TABLE>

STATISTICAL NOTE: CURRENT ANNUALIZED DISTRIBUTION RATE IS THE LATEST MONTHLY
DIVIDEND SHOWN AS AN ANNUALIZED PERCENTAGE OF NET ASSET VALUE/MARKET PRICE ON
THE DATE SHOWN. DISTRIBUTION RATE SIMPLY MEASURES THE LEVEL OF DIVIDENDS AND IS
NOT A COMPLETE MEASURE OF PERFORMANCE. TOTAL RETURN MEASURES AGGREGATE CHANGE IN
NET ASSET VALUE/MARKET PRICE ASSUMING REINVESTMENT OF DIVIDENDS. RETURNS ARE
HISTORICAL AND DO NOT GUARANTEE FUTURE RESULTS. MARKET PRICE, NET ASSET VALUE,
DISTRIBUTION RATES AND RETURNS ARE HISTORICAL AND WILL FLUCTUATE. ADDITIONAL
INFORMATION CONCERNING PERFORMANCE IS CONTAINED IN THE FINANCIAL HIGHLIGHTS
APPEARING AT THE END OF THIS REPORT.


TERMS TO KNOW

BASIS POINT The movement of interest rates or yields expressed in hundredths of
a percent. For example, an increase in yield from 5 percent to 6 percent is 100
basis points.
CREDIT SPREAD The difference in yields between higher-quality and lower-quality
bonds, typically comparing the same types of bonds. For example, if AAA-rated
corporate bonds yield 5 percent, and BBB-rated corporate bonds yield 6 percent,
the credit spread is 1 percent. When the spread becomes less because the higher
yield drops or the lower yield rises, the spread is said to narrow. When the
opposite occurs, the spread is said to widen.

DEFAULT Failure of a borrower to pay what is owed when it is owed. The default
rate of high-yield bonds can be measured as the percentage of bond issuers who
are not meeting their obligations at a given point in time.

FEDERAL FUNDS RATE The interest rate that banks charge each other on overnight
loans. The Federal Reserve Board's Open Market Committee sets a target rate to
either make credit more easily available or tighten monetary policy in an
attempt to avoid economic imbalances such as high inflation.

INVERTED YIELD CURVE A market phenomenon in which intermediate-term bonds
(securities with two- to 10-year maturities) have higher income potential and
current yields than long-term bonds (securities with 10- to 30-year maturities).
Historically it has occurred during a period of rising short-term interest rates
and been viewed as an indicator of a future economic slowdown.


<PAGE>   3
ECONOMIC OVERVIEW

SCUDDER KEMPER INVESTMENTS, THE INVESTMENT MANAGER FOR KEMPER FUNDS, IS ONE OF
THE LARGEST AND MOST EXPERIENCED INVESTMENT MANAGEMENT ORGANIZATIONS IN THE
WORLD, MANAGING MORE THAN $290 BILLION IN ASSETS FOR INSTITUTIONAL AND CORPORATE
CLIENTS, RETIREMENT AND PENSION PLANS, INSURANCE COMPANIES, MUTUAL FUND
INVESTORS AND INDIVIDUALS. SCUDDER KEMPER INVESTMENTS OFFERS A FULL RANGE OF
INVESTMENT COUNSEL AND ASSET MANAGEMENT CAPABILITIES BASED ON A COMBINATION OF
PROPRIETARY RESEARCH AND DISCIPLINED, LONG-TERM INVESTMENT STRATEGIES.

DEAR KEMPER FUNDS SHAREHOLDER,

When an irresistible force such as the ebullient U.S. economy meets an immovable
object, such as a determined Federal Reserve Board, the old song is right:
Something's gotta give. One possibility -- the economy could slow down as the
Fed has ordered. Or, if market volatility becomes true distress, the Fed could
back off, as it has in the past. A third possibility is that neither the Fed nor
the economy will give way until it's too late, which could lead to a recession.
Recent evidence suggests, however, that the economy probably will slow down as
ordered.

  Before explaining why, perhaps it's best to start with a review of how
monetary policy works. Central bankers often sound like witch doctors reading
animal entrails, so it's understandable that many people are confused about
monetary policy. But monetary policy still works in the same way it always has.
First, it changes the price and availability of money. More subtly, it alters
people's perceptions about and confidence in the future, thereby adjusting their
willingness to take risks.

  It's a bit early to tell how the Fed's monetary policy is working so far. The
policymakers only started raising interest rates about a year ago, and it takes
at least that long for higher rates to impact borrowers. There are two reasons.
First, interest rates on many existing loans are fixed. And, a family who has
just selected a dream house isn't going to walk away if mortgage rates rise a
notch. Similarly, a company that has just approved an expansion program won't
stop cold because the prime rate is higher. So it's foolish to think that
America's economy has become less interest-sensitive because the economy roared
through the first several months of this year. Americans are more in hock than
ever, so higher interest rates will hurt more than ever. The May dip in housing
starts and auto sales -- especially the higher priced, gas guzzling sport
utility vehicles -- is probably the first sign that higher rates are biting.
They will bite harder in coming months. We look for both housing starts and
vehicle sales to drop about 10 percent in 2001.

  Confidence is harder to measure, but there are some early flutters of
weakness. It's true that consumers remain cheerily upbeat. But corporate bond
markets, the most sensitive barometer of business confidence and a vital source
of corporate funds, have been nervous. Investors are demanding a big premium
before they'll buy lower quality bonds, which means there's less new money for
companies to spend. Corporate bond issuance through mid-June was 35 percent
below the first five and a half months of 1999.

  So far, companies have been able to get around the bond market stinginess by
turning to their bankers. Banks lent businesses 8 percent more from January
through May of this year than they did during the first five months of 1999. But
some banks are beginning to worry, too. Bank examiners have been questioning the
quality of loans and the level of reserves. In response, more bankers are
tightening lending standards and raising rates. This is a textbook case of how
tighter monetary policy eventually slows an economy.

  Aren't bond market and banker concerns overdone? As long as the economy keeps
growing at 3 percent or so, won't that guarantee such good profits that paying
the bills will be a cinch? Not necessarily. Profits are far more cyclical than
economic growth. Earnings actually fell during 1998, even though the economy
continued to roll. That was a global crisis, when foreign earnings fell sharply.
But take a look at the last "soft landing" during 1995. Revenue growth dipped
and pricing power fell, squeezing profits. The same thing is likely to happen
again in the coming slowdown -- and this time, tight labor markets could make it
even tougher for companies to control costs quickly. Assuming growth is between
2.5 percent and 3 percent by the end of 2001, we believe year-over-year profit
comparisons will have turned slightly negative.

  A profit slowdown when new lines of credit are hard to come by will take its
toll on capital spending. We expect growth in business outlays for buildings and
equipment to slip from over 12 percent this year to around 8 percent in 2001.
That's still quite robust, and the "high-tech imperative" is the reason why.
Executives believe that they have no option but to keep up with the
technological revolution that is transforming the world. The fact that high-tech
gear keeps getting cheaper year after year and also helps save on expensive
labor makes the decision to buy it easy. Indeed, unit sales of computers and
peripherals to businesses have sustained growth rates in excess of 40 percent
since 1995. And the rush is on to lay down the infrastructure for the next
generation of wireless communications. We estimate that the sector will see unit
growth of about 50 percent this year, double the growth in 1999. It's hard even
for superstars to sustain these stratospheric

                                                                               3
<PAGE>   4
ECONOMIC OVERVIEW

 ECONOMIC GUIDEPOSTS

   ECONOMIC ACTIVITY IS A KEY INFLUENCE ON INVESTMENT PERFORMANCE AND
   SHAREHOLDER DECISION-MAKING. PERIODS OF RECESSION OR BOOM, INFLATION OR
   DEFLATION, CREDIT EXPANSION OR CREDIT CRUNCH HAVE A SIGNIFICANT IMPACT ON
   MUTUAL FUND PERFORMANCE.
       THE FOLLOWING ARE SOME SIGNIFICANT ECONOMIC GUIDEPOSTS AND THEIR
   INVESTMENT RATIONALE THAT MAY HELP YOUR INVESTMENT DECISION-MAKING. THE
   10-YEAR TREASURY RATE AND THE PRIME RATE ARE PREVAILING INTEREST RATES.
   THE OTHER DATA REPORT YEAR-TO-YEAR PERCENTAGE CHANGES.
   [BAR GRAPH]

<TABLE>
<CAPTION>
                                           NOW (5/31/00)           6 MONTHS AGO            1 YEAR AGO            2 YEARS AGO
                                           -------------           ------------            ----------            -----------
<S>                                     <C>                    <C>                    <C>                    <C>
10-year Treasury rate (1)                       6.40                   6.00                   5.50                   5.60
Prime rate (2)                                  9.50                   8.50                   7.75                   8.50
Inflation rate (3)*                             3.00                   2.60                   2.30                   1.50
The U.S. dollar (4)                             4.30                  -0.70                  -0.90                   6.40
Capital goods orders (5)*                      17.00                  12.30                   2.50                  14.50
Industrial production (5)*                      6.10                   3.70                   2.90                   5.20
Employment growth (6)                           2.60                   2.20                   2.30                   2.60
</TABLE>

(1) FALLING INTEREST RATES IN RECENT YEARS HAVE BEEN A BIG PLUS FOR FINANCIAL
    ASSETS.
(2) THE INTEREST RATE THAT COMMERCIAL LENDERS CHARGE THEIR BEST BORROWERS.
(3) INFLATION REDUCES AN INVESTOR'S REAL RETURN. IN THE LAST FIVE YEARS,
    INFLATION HAS BEEN AS HIGH AS 6 PERCENT. THE LOW, MODERATE INFLATION OF THE
    LAST FEW YEARS HAS MEANT HIGH REAL RETURNS.
(4) CHANGES IN THE EXCHANGE VALUE OF THE DOLLAR IMPACT U.S. EXPORTERS AND THE
    VALUE OF U.S. FIRMS' FOREIGN PROFITS.
(5) THESE INFLUENCE CORPORATE PROFITS AND EQUITY PERFORMANCE.
(6) AN INFLUENCE ON FAMILY INCOME AND RETAIL SALES.
*DATA AS OF 4/30/00.

SOURCE: ECONOMICS DEPARTMENT, SCUDDER KEMPER INVESTMENTS, INC.

compound growth rates forever, and we do expect some moderation next year.
However, high-tech orders continue to ratchet upwards, and the shortage in
semiconductors and other components has persisted long enough to cause major
players to announce huge capacity additions.

  Another battle the Fed must win before it succeeds in slowing the economy is
bringing consumers to heel. Most families still feel better off than they were
last year and much richer than they were five years ago. That's a powerful
incentive to spend and enjoy. Indeed, total real consumption has been galloping
at a 5 percent rate or better since early 1998. But consumers are so important
to the economy that if they don't start spending less freely, there won't be a
slowdown. We expect the Fed to be successful and slow down shoppers in the
months ahead -- but the victory won't be an easy one. We expect at least one
more rate hike and a few more financial fireworks before consumers and the
economy hoist the white flag.

  So what will the slowdown look like? During the spring, retail sales, housing
starts and job creation slowed, but strength in high tech orders and capital
equipment production probably will help keep the slowdown from becoming too
abrupt. We expect about 3.5 percent growth in the second half. That would still
produce a hearty 5 percent growth for full year 2000. During 2001, the full
impact of the Fed's recent tightening will probably rein growth in to just 3
percent.

Sincerely,

Scudder Kemper Investments Economics Group

THE INFORMATION CONTAINED IN THIS PIECE HAS BEEN TAKEN FROM SOURCES BELIEVED TO
BE RELIABLE, BUT THE ACCURACY OF THE INFORMATION IS NOT GUARANTEED. THE OPINIONS
AND FORECASTS EXPRESSED ARE THOSE OF THE ECONOMIC ADVISORS OF SCUDDER KEMPER
INVESTMENTS, INC. AS OF JUNE 29, 2000, AND MAY NOT ACTUALLY COME TO PASS. THIS
INFORMATION IS SUBJECT TO CHANGE. NO PART OF THIS MATERIAL IS INTENDED AS AN
INVESTMENT RECOMMENDATION.

TO OBTAIN A KEMPER FUNDS PROSPECTUS, DOWNLOAD ONE FROM WWW.KEMPER.COM, TALK TO
YOUR FINANCIAL REPRESENTATIVE OR CALL SHAREHOLDER SERVICES AT (800) 621-1048.
THE PROSPECTUS CONTAINS MORE COMPLETE INFORMATION, INCLUDING MANAGEMENT FEES AND
EXPENSES. PLEASE READ IT CAREFULLY BEFORE YOU INVEST OR SEND MONEY.

 4
<PAGE>   5

MANAGEMENT TEAM

                         KEMPER STRATEGIC INCOME TRUST

                           PORTFOLIO MANAGEMENT TEAM

[J. PATRICK BIEMFORD, JR. PHOTO]
J. PATRICK BEIMFORD JR. JOINED SCUDDER KEMPER INVESTMENTS, INC. IN 1976 AND IS A
MANAGING DIRECTOR AND LEAD PORTFOLIO MANAGER OF KEMPER STRATEGIC INCOME TRUST.
HE IS A CHARTERED FINANCIAL ANALYST.

[ROBERT CESSINE PHOTO]
ROBERT CESSINE IS A MANAGING DIRECTOR OF SCUDDER KEMPER INVESTMENTS, INC. AND
PORTFOLIO MANAGER OF KEMPER STRATEGIC INCOME TRUST. HE JOINED THE COMPANY IN
1993. HE IS A CHARTERED FINANCIAL ANALYST.

[DAN DOYLE PHOTO]
DAN DOYLE IS A FIRST VICE PRESIDENT OF SCUDDER KEMPER INVESTMENTS, INC. AND A
HIGH-YIELD BOND TRADER. HE IS A CHARTERED FINANCIAL ANALYST.

[RICHARD VANDENBERG PHOTO]
RICHARD VANDENBERG, WITH MORE THAN 25 YEARS OF INVESTMENT MANAGEMENT EXPERIENCE,
IS A MANAGING DIRECTOR OF SCUDDER KEMPER INVESTMENTS, INC. AND IS LEAD PORTFOLIO
MANAGER OF SCUDDER KEMPER'S FIXED-INCOME GOVERNMENT AND MORTGAGE FUNDS.

THE VIEWS EXPRESSED IN THIS REPORT REFLECT THOSE OF THE PORTFOLIO MANAGERS ONLY
THROUGH THE END OF THE PERIOD OF THE REPORT AS STATED ON THE COVER. THE
MANAGERS' VIEWS ARE SUBJECT TO CHANGE AT ANY TIME, BASED ON MARKET AND OTHER
CONDITIONS.

                                                                               5
<PAGE>   6

PERFORMANCE UPDATE

PRESERVING CAPITAL PROVED CHALLENGING AS DOMESTIC BONDS FACED A SUBSTANTIAL
TIGHTENING IN FEDERAL RESERVE MONETARY POLICY. EMERGING-MARKET BONDS PROVIDED
STRONG RETURNS SINCE NOVEMBER FOR INVESTORS WILLING TO ASSUME HIGHER RISKS.

Q     HOW DID GLOBAL FIXED-INCOME MARKETS BEHAVE AND KEMPER STRATEGIC INCOME
TRUST PERFORM DURING THE FIRST HALF OF FISCAL YEAR 2000?

A     The period between November 30, 1999, and May 31, 2000, was a challenging
time for fixed-income investors around the world. Emerging-market bonds were the
trust's bright spot, as returns from domestic high-yield bonds were weak. In
most established bond markets, returns for the first half of fiscal year 2000
were disappointing. For the trust, preserving capital was challenging as the
Federal Reserve tightened monetary policy.

  Kemper Strategic Income Trust's 2.06 percent total return (at net asset value)
for the six months ended May 31 outpaced both the average 0.66 percent return of
the trust's Lipper peers (closed-end flexible income funds) and the 1.47 percent
return of the trust's unmanaged benchmark, the Lehman Brothers
Government/Corporate index, a group of investment-grade bonds that vary in
maturity and quality.

Q     HIGH-YIELD BONDS WERE A SIGNIFICANT COMPONENT OF THE PORTFOLIO DURING THE
FIRST HALF OF FISCAL YEAR 2000. COULD YOU ELABORATE ON MARKET CONDITIONS IN THE
HIGH-RISK DEBT MARKET SINCE NOVEMBER?

A     The returns from high-yield bonds were modest for the six months ended May
31, 2000. The total return of the unmanaged Merrill Lynch High Yield Master
index, a group of lower-rated bonds that vary in quality, was -2.28 percent for
the period. The price component of the index fell 6.59 percent. For many
high-yield investors, preserving capital was a challenge, as income did not
offset losses in principal value.

  One reason for the high-yield market's weakness was anemic investor demand.
This past winter, the lure of potentially higher returns from equity
investments, particularly technology stocks, prompted some investors to
liquidate high-yield holdings and redeploy assets. As the U.S. economy enjoyed
solid growth, some investors behaved as if high-yield bonds faced the worst of
times. Ironically, in January, February, April and May, high-yield bonds
outperformed the unmanaged Standard & Poor's 500 stock index.

Q     COULD YOU DESCRIBE HOW THE TRUST'S HIGH-YIELD BONDS WERE POSITIONED DURING
THE PERIOD?

A     In a difficult environment, we believed success depended on not losing
sight of the fact that the underpinnings of the high-yield debt market were
sound. Since mid-1999, commodity prices have rebounded, helping many
"old-economy" companies meet debt payments. During the period, we focused on
larger, more liquid bond issues, and on companies with relatively solid cash
flow and proven management.

  Since November 1999, the difference in yield, or spread, between 10-year
Treasuries and comparable-maturity high-yield bonds widened to 678 basis points
(6.78 percent). Given that 10-year Treasury bonds yielded 6.27 percent at the
end of May 2000, high-yield bonds offered double the yield of government bonds
for investors willing to assume additional risk. That's why we had a majority of
the trust's assets in the high-yield category.

Q     WHAT HAS BEEN THE HISTORICAL EXPERIENCE OF THE HIGH-YIELD BOND MARKET
DURING PERIODS OF STOCK MARKET WEAKNESS?

A     For seven times since October 1987, high-yield bonds outperformed the
Standard & Poor's 500 stock index (S&P 500) during months when the S&P 500
declined 5 percent or more. While we can't say this pattern will continue, we
believe that high-yield bonds deserve a place in a well-balanced portfolio now
more than ever. After five years of strong equity market performance, many
investors have portfolios that are heavily laden with large-cap stocks. We think
it would be a mistake for investors to overlook the opportunity to maintain the
diversification that this asset class offers.

Q     HOW HAVE OTHER TYPES OF DOMESTIC BONDS FARED SINCE NOVEMBER?

A     Strong economic growth prompted the Federal Reserve to raise its
short-term interest-rate target three times since November by a total of 100
basis points (1 percent) to 6.50 percent. This past winter, the government also
announced a buyback plan for 30-year Treasuries. These two events decreased the
attractiveness of most

 6
<PAGE>   7
PERFORMANCE UPDATE

types of intermediate-term (two- to 10-year) bonds. Prices of intermediate,
investment-grade corporate bonds and other non-Treasury debt such as mortgages
generally fell. GNMA mortgages generally outperformed FNMA mortgages for most of
the period. Overall, the Lehman Brothers U.S. Agency index rose 0.87 percent for
the six months ended May 31, 2000.

Q     YOU SAID THAT EMERGING-MARKET BONDS WERE THE PORTFOLIO'S BRIGHT SPOT. HOW
WELL HAVE THEY DONE AND WHY?

A     Investors are expecting that growth will pick up steam in emerging markets
in the coming months. Bonds in some countries such as Mexico have rallied since
November as rating services have upgraded certain government debt to
investment-grade. The trust benefited from this trend because we had made Mexico
one of the trust's largest emerging-market holdings. Overall, the Lehman
Brothers Emerging Markets Bond index rose 7.50 percent for the six months ended
May 31, 2000. The index is an unmanaged group of higher-risk overseas debt
issued by governments and corporations in either U.S. dollars or local
currencies.

Q     FINALLY, HOW ARE YOU POSITIONING THE PORTFOLIO FOR THE ROAD AHEAD?

A     At some point, we believe there is potential for equity-like returns from
domestic high-yield securities and higher prices for most categories of U.S. and
overseas bonds. First, however, the Fed needs to be convinced that domestic
inflation will not become problematic. This would help alleviate the need for
emerging-market countries to raise interest rates to match the Fed and protect
the purchasing power of their currencies.

  Although we think short-term bond market volatility may continue for the rest
of fiscal year 2000, some long-term positive trends are in place. A robust U.S.
economy and a recovering global economy are helping debtors meet their bond
obligations.

  We are confident in the long-term soundness of our investment strategy, and we
believe investors share that confidence, given the fact that the trust sold at a
more than 10 percent premium to its net asset value as of May 31, 2000. Today's
exceptionally dynamic global bond market environment demands patience from
fixed-income investors, and we appreciate the confidence that investors have
shown in our team.

  HIGH-YIELD BOND PERFORMANCE VS. S&P 500 INDEX
During months when the S&P 500 index declined by 5 percent 1987 to 2000.

[BAR CHART]
<TABLE>
<CAPTION>

               Merrill Lynch High Yield Master Index II*         S&P 500 Index
               -----------------------------------------         -------------
<S>            <C>                                               <C>
10/87                         -2.67%                                 -21.53%
11/87                          2.53%                                  -8.24%
1/90                          -1.95%                                  -6.71%
8/90                          -3.83%                                  -9.03%
8/97                          -0.17%                                  -5.60%
8/98                          -4.32%                                 -14.45%
1/00                          -0.38%                                  -5.02%
</TABLE>

*THE MERRILL LYNCH HIGH YIELD MASTER INDEX II IS AN UNMANAGED GROUP OF LOWER
QUALITY BONDS THAT VARY IN MATURITY AND QUALITY.

SOURCES: BLOOMBERG BUSINESS NEWS AND MERRILL LYNCH

                                                                               7
<PAGE>   8

PORTFOLIO STATISTICS

PORTFOLIO COMPOSITION*

<TABLE>
<CAPTION>
                                      ON 5/31/00              ON 11/30/99
<S> <C>                               <C>                     <C>         <C>
    GNMA AND OTHER MORTGAGES              30%                      28%
 ................................................................................
    HIGH-YIELD CORPORATE BONDS            18                       21
 ................................................................................
    EMERGING MARKET BONDS                 48                       49
 ................................................................................
    OTHER                                  4                        2
--------------------------------------------------------------------------------
                                         100%                     100%
</TABLE>

[PIE CHART] [PIE CHART]

LONG-TERM FIXED INCOME SECURITIES RATINGS+

<TABLE>
<CAPTION>
                                      ON 5/31/00              ON 11/30/99
<S> <C>                               <C>                     <C>         <C>
    AAA                                   36%                      29%
 ................................................................................
    BBB                                    6                       --
 ................................................................................
    BB                                    14                       29
 ................................................................................
    B                                     40                       32
 ................................................................................
    OTHER                                  4                       10
--------------------------------------------------------------------------------
                                         100%                     100%
</TABLE>

+THE RATINGS OF STANDARD AND POOR'S CORPORATION (S&P) AND MOODY'S INVESTORS
 SERVICES, INC. (MOODY'S) REPRESENT THEIR OPINIONS AS TO THE QUALITY OF
 SECURITIES THAT THEY UNDERTAKE TO RATE. THE PERCENTAGE SHOWN REFLECTS THE
 HIGHER OF S&P OR MOODY'S RATINGS. PORTFOLIO COMPOSITION WILL CHANGE OVER TIME.
 RATINGS ARE RELATIVE AND SUBJECTIVE AND NOT ABSOLUTE STANDARDS OF QUALITY.

[PIE CHART] [PIE CHART]

AVERAGE MATURITY

<TABLE>
<CAPTION>
                                      ON 5/31/00              ON 11/30/99
<S> <C>                               <C>                     <C>         <C>
    AVERAGE MATURITY                  8.10 years              8.01 years
--------------------------------------------------------------------------------
</TABLE>

*PORTFOLIO COMPOSITION IS SUBJECT TO CHANGE.

 8
<PAGE>   9

PORTFOLIO OF INVESTMENTS

KEMPER STRATEGIC INCOME TRUST
Portfolio of Investments at May 31, 2000 (Unaudited)

<TABLE>
<CAPTION>
    REPURCHASE AGREEMENT--0.3%                                                        PRINCIPAL AMOUNT      VALUE
<S> <C>                                   <C>                                         <C>                <C>         <C>
                                          State Street Bank and Trust Company,
                                            6.37%, to be repurchased at $175,031 on
                                            06/01/2000(b)
                                            (Cost: $175,000)                            $   175,000      $   175,000
                                           ------------------------------------------------------------------------------

    SHORT-TERM OBLIGATION--4.5%

                                          Student Loan Marketing Association, 6.30%,
                                            06/01/2000
                                            (Cost: $2,500,000)                            2,500,000        2,500,000
                                          ------------------------------------------------------------------------------

    U.S. GOVERNMENT AGENCY PASS-THRUS--29.5%

                                          Federal National Mortgage Association
                                            7.50% with various maturities to
                                             04/01/2027                                     628,789          611,891
                                            7.00% with various maturities to
                                             08/01/2027                                     543,836          517,324
                                          Government National Mortgage Association
                                            8.00% with various maturities to 9/15/2026    5,237,460        5,264,663
                                            7.50% with various maturities to
                                             07/15/2029                                   9,610,356        9,459,123
                                            7.00% with various maturities to
                                             06/15/2029                                     743,364          713,165
                                          ------------------------------------------------------------------------------
                                          TOTAL U.S. GOVERNMENT AGENCY PASS-THRUS
                                          (Cost: $16,445,117)                                             16,566,166
                                          ------------------------------------------------------------------------------

    FOREIGN BONDS--47.6%

                                          Federative Republic of Brazil C Bond,
                                            8.00%, 04/15/2014(c)                         17,003,328       11,923,584
                                          Republic of Argentina:
                                            6.178%, 09/01/2002(c)                         6,969,850        6,585,337
                                            6.178%, 04/01/2007(c)                         4,691,389        3,856,313
                                          Republic of Panama, Floating Rate Note,
                                            LIBOR plus 1%, 7.00%, 05/10/2002(c)             869,300          853,001
                                          Republic of Venezuela, Debt Conversion
                                            Bond, Floating Rate Bond, Series DL,
                                            LIBOR plus .875%, 7.00%, 12/18/2007(c)          571,429          449,286
                                          United Mexican States, Collateralized Par
                                            Bond, Series A, 6.25% 12/31/2019              2,500,000        1,993,750
                                          United Mexican States, 11.50%, 05/15/2026         910,000        1,020,337
                                          ------------------------------------------------------------------------------
                                          TOTAL FOREIGN BONDS
                                          (Cost: $23,728,876)                                             26,681,608
                                          ------------------------------------------------------------------------------
</TABLE>

    The accompanying notes are an integral part of the financial statements.   9
<PAGE>   10

PORTFOLIO OF INVESTMENTS

<TABLE>
<CAPTION>
    CORPORATE BONDS--18.0%                                                            PRINCIPAL AMOUNT      VALUE
<S> <C>                                   <C>                                         <C>                <C>         <C>

    CONSUMER
    DISCRETIONARY--2.2%
                                          Advantica Restaurant Co., 11.25%,
                                            01/15/2008                                  $    50,000      $    33,250
                                          Boca Resorts, Inc., 9.875%, 04/15/2009            250,000          231,250
                                          Color Tile, Inc., 10.75%, 12/15/2001*             330,000            3,300
                                          Hines Horticulture, Inc., 11.75%,
                                            10/15/2005                                      325,000          325,812
                                          National Vision Association, Ltd.,
                                            12.750%, 10/15/2005*                            510,000          173,400
                                          Players International, 10.875%, 04/15/2005        470,000          487,625
                                          ------------------------------------------------------------------------------
                                                                                                           1,254,637
------------------------------------------------------------------------------------------------------------------------

    CONSUMER STAPLES--0.1%
                                          Jafra Cosmetics International, Inc.,
                                            11.75%, 05/01/2008                               40,000           38,400
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    COMMUNICATIONS--6.9%
                                          Allegiance Telecom, Inc., 12.875%,
                                            05/15/2008                                      390,000          417,300
                                          Call-Net Enterprises, Inc., Step-up
                                            Coupon, 0% to 05/15/2004, 10.80% to
                                            05/15/2009,                                     150,000           48,000
                                            9.375%, 05/15/2009                              100,000           58,000
                                          Intermedia Communications of Florida,
                                            Inc., Step-up Coupon, 0% to 07/15/2002,
                                            11.25% to 07/15/2007                            520,000          386,100
                                          KMC Telecom Holdings, Inc., 13.50%,
                                            05/15/2009                                      100,000           87,000
                                          Level 3 Communications Inc., 11.250%,
                                            03/15/2010                                       20,000           19,000
                                            9.125%, 05/01/2008                               10,000            8,625
                                          MGC Communications, 13.000%, 10/01/2004           350,000          364,875
                                          MetroNet Communications Corp., 12.00%,
                                            08/15/2007                                      100,000          110,750
                                          Millicom International Cellular, S.A.,
                                            Step-up Coupon, 0% to 06/01/2001,
                                            13.50% to 06/01/2006                            460,000          384,100
                                          Nextlink Communications, Inc., 10.75%,
                                            11/15/2008                                      140,000          134,400
                                          PTC International Finance,
                                            Step-up Coupon, 0% to 07/01/2002,
                                            10.75% to 07/01/2007                            500,000          345,000
                                          Teligent, Inc., 11.500%, 12/01/2007               250,000          188,750
                                          Triton Communications, L.L.C.,
                                            Step-up Coupon, 0% to 05/01/2003,
                                            11.00% to 05/01/2008                            200,000          144,500
                                          U.S. Xchange, L.L.C., 15.00%, 07/01/2008          370,000          403,300
                                          USA Mobile Communications Holdings, Inc.,
                                            14.00%, 11/01/2004                               60,000           50,400
                                          Viatel, Inc., Step-up Coupon, 0% to
                                            04/15/2003, 12.50% to 04/15/2008                450,000          225,000
                                          Western Wireless Corp., 10.50%, 02/01/2007        440,000          464,200
                                          ------------------------------------------------------------------------------
                                                                                                           3,839,300
------------------------------------------------------------------------------------------------------------------------

    FINANCIAL--0.7%
                                          Spectrasite Holdings, Inc., Step-up
                                            Coupon, 0% to 07/15/2003, 12.000% to
                                            07/15/2008                                       50,000           31,500
                                            0% to 04/15/2004, 11.250% to 04/15/2009         670,000          358,450
                                          ------------------------------------------------------------------------------
                                                                                                             389,950
------------------------------------------------------------------------------------------------------------------------

    MEDIA--3.3%
                                          Australis Holdings, Step-up Coupon, 0% to
                                            11/01/2000, 15.00% to 11/01/2002*               500,000            5,000
                                            Zero coupon, 11/01/2000                          15,515           11,791
                                            CSC Holdings, Inc., 9.875%, 02/15/2013          450,000          444,375
</TABLE>

 10 The accompanying notes are an integral part of the financial statements.
<PAGE>   11

PORTFOLIO OF INVESTMENTS

<TABLE>
<CAPTION>
                                                                                      PRINCIPAL AMOUNT      VALUE
<S> <C>                                   <C>                                         <C>                <C>         <C>
                                          Diamond Cable Communications, PLC,
                                            Step-up Coupon, 0% to
                                            12/15/2000, 11.75% to 12/15/2005            $   175,000      $   163,625
                                          Frontiervision LP, 11.00%, 10/15/2006             400,000          401,000
                                          NTL Communications Corp.,
                                            Step-up Coupon 0% to
                                            10/01/2003, 12.375% to 10/01/2008               500,000          320,000
                                          NTL, Inc., 11.50%, 10/01/2008                     320,000          321,600
                                          Sinclair Broadcasting Group, Inc., 8.75%,
                                            12/15/2007                                      250,000          207,500
                                          ------------------------------------------------------------------------------
                                                                                                           1,874,891
------------------------------------------------------------------------------------------------------------------------

    SERVICE INDUSTRIES--0.8%
                                          Coinmach Corp., 11.75%, 11/15/2005                500,000          460,000
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    DURABLES--0.2%
                                          Fairchild Corp., 10.75%, 04/15/2009               130,000           85,800
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    MANUFACTURING--2.1%
                                          Day International Group, Inc., 11.125%,
                                            06/01/2005                                       35,000           35,000
                                          GS Technologies, 12.25%, 10/01/2005               100,000           40,000
                                          Gaylord Container Corp.,
                                            9.875%, 02/15/2008                               40,000           29,600
                                            9.75%, 06/15/2007                                70,000           59,500
                                          Huntsman Package, 11.75%, 12/01/2004              170,000          171,700
                                          Riverwood International Corp., 10.875%,
                                            04/01/2008                                      830,000          771,900
                                          Stone Container Corp., 11.50%, 08/15/2006          70,000           72,800
                                          ------------------------------------------------------------------------------
                                                                                                           1,180,500
------------------------------------------------------------------------------------------------------------------------

    ENERGY--0.1%
                                          R&B Falcon Corp., 9.50%, 12/15/2008                60,000           58,800
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    METALS & MINERALS--0.8%
                                          Euramax International, PLC, 11.25%,
                                            10/01/2006                                      400,000          384,000
                                          Republic Technologies International,
                                            13.75%, 07/15/2009                              510,000           63,750
                                          ------------------------------------------------------------------------------
                                                                                                             447,750
------------------------------------------------------------------------------------------------------------------------

    CONSTRUCTION--0.6%
                                          Dimac Corp., 12.500%, 10/01/2008                  600,000            6,000
                                          Hovnanian Enterprises, Inc., 9.75%,
                                            06/01/2005                                       10,000            8,875
                                          Lennar Corp., 7.625%, 03/01/2009                  100,000           84,000
                                          Nortek, Inc., 9.875%, 03/01/2004                  270,000          254,475
                                          ------------------------------------------------------------------------------
                                                                                                             353,350
------------------------------------------------------------------------------------------------------------------------

    MISCELLANEOUS--0.2%
                                          FairPoint Communications, Inc., 12.50%,
                                            05/01/2010                                      100,000          100,500
                                          ------------------------------------------------------------------------------
                                          TOTAL CORPORATE BONDS
                                          (Cost: $12,803,148)                                             10,083,878
                                          ------------------------------------------------------------------------------
</TABLE>

    The accompanying notes are an integral part of the financial statements.  11
<PAGE>   12

PORTFOLIO OF INVESTMENTS

<TABLE>
<CAPTION>
                                                                                         NUMBER OF
    COMMON STOCK--.0%                                                                      SHARES           VALUE
<S> <C>                                   <C>                                         <C>                <C>         <C>

    COMMUNICATIONS--0.0%
                                          AT&T Canada Inc.*                                     342      $    13,338
                                          ------------------------------------------------------------------------------
    RIGHTS & WARRANTS*--.1%

    COMMUNICATIONS--0.1%
                                          Intermedia Communications of Florida, Inc.            200           32,000
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    MEDIA--0.0%
                                          UIH Australia Pacific, Inc.                           280            8,400
                                          Australis Holdings                                    510                0
                                          ------------------------------------------------------------------------------
                                                                                                               8,400
------------------------------------------------------------------------------------------------------------------------

    ENERGY--0.0%
                                          Empire Gas Corp.                                      359               36
                                          ------------------------------------------------------------------------------
------------------------------------------------------------------------------------------------------------------------

    METALS & MINERALS--0.0%
                                          Gulf States Steel                                     150                2
                                          Republic Technologies International                   510                5
                                          ------------------------------------------------------------------------------
                                                                                                                   7
------------------------------------------------------------------------------------------------------------------------

    MISCELLANEOUS--0.0%
                                          Bar Technologies                                      500           10,000
                                          ------------------------------------------------------------------------------
                                          TOTAL RIGHTS & WARRANTS
                                          (Cost: $31,897)                                                     50,443
                                          ------------------------------------------------------------------------------
                                          TOTAL INVESTMENT PORTFOLIO--100.0%
                                          (Cost: $55,684,038) (a)                                        $56,070,433
                                          ------------------------------------------------------------------------------
</TABLE>

 NOTES TO PORTFOLIO OF INVESTMENTS

 *   Non-income producing security. In the case of a bond, generally denotes
     that the issuer has defaulted on the payment of principal or interest or
     has filed for bankruptcy.

(a)  The cost for federal income tax purposes was $55,684,038. At May 31, 2000,
     net unrealized appreciation for all securities based on tax cost was
     $386,395. This consisted of aggregate gross unrealized appreciation for all
     securities in which there was an excess of market value over tax cost of
     $3,387,004 and aggregate gross unrealized depreciation for all securities
     in which there was an excess of tax cost over market value of $3,000,609.

(b)  Repurchase agreements are fully collateralized by U.S. Treasury or
     Government agency securities.

(c)  Variable rate security. Rate shown is the effective rate on May 31, 2000
     and the date shown represents the final maturity of the obligation.

 12 The accompanying notes are an integral part of the financial statements.
<PAGE>   13

FINANCIAL STATEMENTS

STATEMENT OF ASSETS AND LIABILITIES
As of May 31, 2000 (Unaudited)

<TABLE>
<S>                                                             <C>
ASSETS
Investments in securities, at value (cost $55,684,038)          $56,070,433
---------------------------------------------------------------------------
Receivable for investments sold                                       7,744
---------------------------------------------------------------------------
Interest receivable                                                 612,454
---------------------------------------------------------------------------
TOTAL ASSETS                                                     56,690,631
---------------------------------------------------------------------------
 LIABILITIES
Due to custodian bank                                               497,330
---------------------------------------------------------------------------
Payable for investments purchased                                     7,694
---------------------------------------------------------------------------
Liability under reverse of repurchase agreements                 13,318,000
---------------------------------------------------------------------------
Interest payable                                                    169,265
---------------------------------------------------------------------------
Accrued management fee                                               31,202
---------------------------------------------------------------------------
Other accrued expenses                                               51,579
---------------------------------------------------------------------------
Total liabilities                                                14,075,070
---------------------------------------------------------------------------
NET ASSETS, AT VALUE                                            $42,615,561
---------------------------------------------------------------------------
 NET ASSETS
Net assets consist of:
Undistributed net investment income (loss)                      $   241,115
---------------------------------------------------------------------------
Net unrealized appreciation (depreciation) on investment
securities                                                          386,395
---------------------------------------------------------------------------
Accumulated net realized gain (loss)                             (6,253,103)
---------------------------------------------------------------------------
Paid-in capital                                                  48,241,154
---------------------------------------------------------------------------
NET ASSETS, AT VALUE                                            $42,615,561
---------------------------------------------------------------------------
 NET ASSET VALUE
NET ASSET VALUE, per share ($42,615,561 / 3,466,478 shares
of beneficial interest, $.01 par value, unlimited number of
shares authorized)                                                   $12.29
---------------------------------------------------------------------------
</TABLE>

    The accompanying notes are an integral part of the financial statements.  13
<PAGE>   14

FINANCIAL STATEMENTS

STATEMENT OF OPERATIONS
Six months ended May 31, 2000 (unaudited)

<TABLE>
<S>                                                             <C>
INVESTMENT INCOME
Interest                                                        $ 3,568,152
---------------------------------------------------------------------------
Dividends                                                                51
---------------------------------------------------------------------------
Total Income                                                      3,568,203
---------------------------------------------------------------------------
Expenses:
Management fee                                                      192,208
---------------------------------------------------------------------------
Services to shareholders                                             13,882
---------------------------------------------------------------------------
Custodian fees                                                        5,411
---------------------------------------------------------------------------
Auditing                                                             19,947
---------------------------------------------------------------------------
Legal                                                                 4,772
---------------------------------------------------------------------------
Trustees' fees and expenses                                           6,222
---------------------------------------------------------------------------
Reports to shareholders                                              35,924
---------------------------------------------------------------------------
Interest expense                                                    411,853
---------------------------------------------------------------------------
Other                                                                23,713
---------------------------------------------------------------------------
Total expenses, before expense reductions                           713,932
---------------------------------------------------------------------------
Expense reductions                                                   (2,165)
---------------------------------------------------------------------------
Total expenses, after expense reductions                            711,767
---------------------------------------------------------------------------
NET INVESTMENT INCOME (LOSS)                                      2,856,436
---------------------------------------------------------------------------
 REALIZED AND UNREALIZED GAIN (LOSS) ON INVESTMENT TRANSACTIONS
Net realized gain (loss) from investments                          (173,064)
---------------------------------------------------------------------------
Net unrealized appreciation (depreciation) during the period
on investment transactions                                       (1,601,357)
---------------------------------------------------------------------------
Net gain (loss) on investment transactions                       (1,774,421)
---------------------------------------------------------------------------
NET INCREASE (DECREASE) IN NET ASSETS RESULTING FROM
OPERATIONS                                                      $ 1,082,015
---------------------------------------------------------------------------
</TABLE>

 14 The accompanying notes are an integral part of the financial statements.
<PAGE>   15

FINANCIAL STATEMENTS

STATEMENTS OF CHANGES IN NET ASSETS

<TABLE>
<CAPTION>
                                                                SIX MONTHS
                                                                   ENDED
                                                                  MAY 31,        YEAR ENDED
                                                                   2000         NOVEMBER 30,
                                                                (UNAUDITED)         1999
<S>                                                             <C>            <C>
INCREASE (DECREASE) IN NET ASSETS
Operations:
Net investment income (loss)                                    $ 2,856,436     $ 5,860,337
---------------------------------------------------------------------------------------------
Net realized gain (loss)                                           (173,064)        346,926
---------------------------------------------------------------------------------------------
Net unrealized appreciation (depreciation) on investment
transactions during the period                                   (1,601,357)     (2,754,248)
---------------------------------------------------------------------------------------------
Net increase (decrease) in net assets resulting from
operations                                                        1,082,015       3,453,015
---------------------------------------------------------------------------------------------
Distributions to shareholders:
From net investment income                                       (3,124,397)     (6,230,795)
---------------------------------------------------------------------------------------------
Fund share transactions:
Reinvestment of distributions                                        39,444          74,399
---------------------------------------------------------------------------------------------
Net increase (decrease) in net assets from Fund share
transactions                                                         39,444          74,399
---------------------------------------------------------------------------------------------
Increase (decrease) in net assets                                (2,002,938)     (2,703,381)
---------------------------------------------------------------------------------------------
Net assets at beginning of period                                44,618,499      47,321,880
---------------------------------------------------------------------------------------------
Net assets at end of period (including undistributed net
investment income of $241,115 and $509,076, respectively)       $42,615,561     $44,618,499
---------------------------------------------------------------------------------------------
 OTHER INFORMATION
Shares outstanding at beginning of period                         3,463,535       3,459,198
---------------------------------------------------------------------------------------------
Shares issued to shareholders in reinvestment of
distributions                                                         2,943           4,337
---------------------------------------------------------------------------------------------
Net increase in Fund Shares                                           2,943           4,337
---------------------------------------------------------------------------------------------
Shares outstanding at end of period                               3,466,478       3,463,535
---------------------------------------------------------------------------------------------
</TABLE>

    The accompanying notes are an integral part of the financial statements.  15
<PAGE>   16

FINANCIAL STATEMENTS

STATEMENT OF CASH FLOWS
Six months ended May 31, 2000 (Unaudited)

<TABLE>
<S>                                                             <C>
CASH FLOWS FROM OPERATING ACTIVITIES
Investment income received                                      $ 2,356,877
---------------------------------------------------------------------------
Payment of operating expenses                                      (671,546)
---------------------------------------------------------------------------
Proceeds from sale and maturities of investments                  4,416,329
---------------------------------------------------------------------------
Purchases of investments                                         (3,583,019)
---------------------------------------------------------------------------
CASH PROVIDED BY OPERATING ACTIVITIES                             2,518,641
---------------------------------------------------------------------------
 CASH FLOWS FROM FINANCING ACTIVITIES
Distributions paid (net of reinvestment of dividends)            (3,084,953)
---------------------------------------------------------------------------
Net increase in liability under reverse repurchase
agreements                                                           34,000
---------------------------------------------------------------------------
Cash provided by financing activities                            (3,050,953)
---------------------------------------------------------------------------
Decrease in cash                                                   (532,064)
---------------------------------------------------------------------------
Cash at beginning of period                                          34,734
---------------------------------------------------------------------------
CASH AT END OF PERIOD                                           $  (497,330)
---------------------------------------------------------------------------
 RECONCILIATION OF NET INCREASE IN NET ASSETS FROM OPERATIONS TO CASH
 PROVIDED BY ACTIVATING ACTIVITIES
Net increase in net assets resulting from operations            $ 1,082,015
---------------------------------------------------------------------------
Net decrease in cost of investments                               1,419,759
---------------------------------------------------------------------------
Decrease in interest receivable                                      30,103
---------------------------------------------------------------------------
Increase in receivable for investments sold                          (7,744)
---------------------------------------------------------------------------
Decrease in payable for investments purchased                       (56,522)
---------------------------------------------------------------------------
Increase in interest payable                                         70,561
---------------------------------------------------------------------------
Decrease in accrued expenses and payables                           (19,531)
---------------------------------------------------------------------------
CASH PROVIDED BY OPERATING ACTIVITIES                           $ 2,518,641
---------------------------------------------------------------------------
</TABLE>

 16 The accompanying notes are an integral part of the financial statements.
<PAGE>   17

FINANCIAL HIGHLIGHTS

THE FOLLOWING TABLES INCLUDE SELECTED DATA FOR A SHARE OUTSTANDING THROUGHOUT
EACH PERIOD AND OTHER PERFORMANCE INFORMATION DERIVED FROM THE FINANCIAL
STATEMENTS AND MARKET PRICE DATA.

<TABLE>
<CAPTION>
                                                     SIX MONTHS
                                                        ENDED
                                                       MAY 31,                YEARS ENDED NOVEMBER 30,
                                                        2000       -----------------------------------------------
                                                     (UNAUDITED)    1999      1998     1997     1996     1995
<S>                                                  <C>           <C>       <C>      <C>      <C>      <C>    <C>
PER SHARE OPERATING PERFORMANCE
------------------------------------------------------------------------------------------------------------------
Net asset value, beginning of year                      $12.88       13.68    15.39    15.34    13.12    12.60
------------------------------------------------------------------------------------------------------------------
Income from investment operations:
Net investment income                                      .82(a)     1.69(a)   1.77    1.79     1.75     1.68
------------------------------------------------------------------------------------------------------------------
Net realized and unrealized gain (loss) on
investment transactions                                   (.51)       (.69)   (1.68)     .06     2.25      .54
------------------------------------------------------------------------------------------------------------------
Total from investment operations                           .31        1.00      .09     1.85     4.00     2.22
------------------------------------------------------------------------------------------------------------------
Less distributions from net investment income             (.90)      (1.80)   (1.80)   (1.80)   (1.78)   (1.70)
------------------------------------------------------------------------------------------------------------------
Net asset value, end of year                            $12.29       12.88    13.68    15.39    15.34    13.12
------------------------------------------------------------------------------------------------------------------
Market value, end of year                               $13.94       14.19    16.94    19.81    17.75    14.25
------------------------------------------------------------------------------------------------------------------
 TOTAL RETURN
------------------------------------------------------------------------------------------------------------------
Based on net asset value (%)                              2.06**      6.03      .48    12.55    32.63    19.29
------------------------------------------------------------------------------------------------------------------
Based on market value (%)                                 5.09**     (5.67)   (5.28)   23.53    39.99    20.70
------------------------------------------------------------------------------------------------------------------
 RATIOS TO AVERAGE NET ASSETS AND SUPPLEMENTAL DATA
------------------------------------------------------------------------------------------------------------------
Net assets at end of year ($ thousands)                 42,616      44,618   47,322   53,129   52,944   44,776
------------------------------------------------------------------------------------------------------------------
Ratio of expenses before expense reductions (%)           3.21*       3.21     3.94     3.99     3.89     4.35
------------------------------------------------------------------------------------------------------------------
Ratio of expenses after expense reductions (%)            3.20*       3.21     3.94     3.99     3.89     4.35
------------------------------------------------------------------------------------------------------------------
Ratio of expenses before interest expense (%)             1.35*       1.40     1.20     1.24     1.23     1.26
------------------------------------------------------------------------------------------------------------------
Ratio of net investment income (%)                       12.85*      12.94    12.05    11.45    12.43    13.56
------------------------------------------------------------------------------------------------------------------
Portfolio turnover rate (%)                                 13*         19       13       16       19       49
------------------------------------------------------------------------------------------------------------------
</TABLE>

NOTE: Total return based on net asset value reflects changes in the Fund's net
asset value during the period. Total return based on market value reflects
changes in market value. Each figure includes reinvestment of dividends. These
figures will differ depending upon the level of any discount from or premium to
net asset value at which the Fund's shares trade during the period.

 * Annualized
** Not annualized
(a) Based on monthly average shares outstanding during the period.

                                                                              17
<PAGE>   18

NOTES TO FINANCIAL STATEMENTS

--------------------------------------------------------------------------------

1    SIGNIFICANT
     ACCOUNTING POLICIES     Kemper Strategic Income Trust (the "Fund"), is
                             registered under the Investment Company Act of
                             1940, as amended (the "1940 Act"), as a closed-end,
                             diversified management investment company organized
                             as a Massachusetts business trust.

                             The Fund's financial statements are prepared in
                             accordance with accounting principles generally
                             accepted in the United States which require the use
                             of management estimates. The policies described
                             below are followed consistently by the Fund in the
                             preparation of its financial statements.

                             SECURITY VALUATION. Investments are stated at value
                             determined as of the close of regular trading on
                             the New York Stock Exchange. Securities which are
                             traded on U.S. or foreign stock exchanges are
                             valued at the most recent sale price reported on
                             the exchange on which the security is traded most
                             extensively. If no sale occurred, the security is
                             then valued at the calculated mean between the most
                             recent bid and asked quotations. If there are no
                             such bid and asked quotations, the most recent bid
                             quotation is used. Securities quoted on the Nasdaq
                             Stock Market ("Nasdaq"), for which there have been
                             sales, are valued at the most recent sale price
                             reported. If there are no such sales, the value is
                             the most recent bid quotation. Securities which are
                             not quoted on Nasdaq but are traded in another
                             over-the-counter market are valued at the most
                             recent sale price, or if no sale occurred, at the
                             calculated mean between the most recent bid and
                             asked quotations on such market. If there are no
                             such bid and asked quotations, the most recent bid
                             quotation shall be used.

                             Portfolio debt securities purchased with an
                             original maturity greater than sixty days are
                             valued by pricing agents approved by the officers
                             of the trust, whose quotations reflect
                             broker/dealer-supplied valuations and electronic
                             data processing techniques. If the pricing agents
                             are unable to provide such quotations, the most
                             recent bid quotation supplied by a bona fide market
                             maker shall be used.

                             Money market instruments purchased with an original
                             maturity of sixty days or less are valued at
                             amortized cost.

                             All other securities are valued at their fair value
                             as determined in good faith by the Valuation
                             Committee of the Board of Trustees.

                             REPURCHASE AGREEMENTS. The Fund may enter into
                             repurchase agreements with certain banks and
                             broker/dealers whereby the Fund, through its
                             custodian or sub-custodian bank, receives delivery
                             of the underlying securities, the amount of which
                             at the time of purchase and each subsequent
                             business day is required to be maintained at such a
                             level that the market value is equal to at least
                             the principal amount of the repurchase price plus
                             accrued interest.

                             REVERSE REPURCHASE AGREEMENTS. The Fund may borrow
                             through the use of reverse repurchase agreements
                             whereby the Fund agrees to sell and simultaneously
                             agrees to repurchase certain securities at a
                             mutually agreed date and price. At the time the
                             Fund enters into a reverse repurchase agreement, it
                             is required to pledge securities subject to
                             repurchase. The sale of these securities is not
                             recorded and the Fund agrees to later repay cash
                             plus interest. Should the securities' value decline
                             below the repurchase price, the Fund may be
                             obligated to pledge additional collateral to the
                             lender in the form of cash or securities. Reverse
                             repurchase agreements involve the risk that the
                             market value of the securities purchased with the
                             proceeds from the sale of securities subject to
                             reverse repurchase agreements may decline below the
                             amount the Fund is

 18
<PAGE>   19

NOTES TO FINANCIAL STATEMENTS

                             obligated to pay to repurchase these securities.
                             The risk in borrowing, as with any extension of
                             credit, consists of the possible delay in the
                             recovery of securities or possible loss of rights
                             in the collateral should the counterparty fail
                             financially. Additionally, there is the risk that
                             the expense associated with the transaction may be
                             greater than the income earned from the investment
                             of the proceeds of the transaction.

                             FEDERAL INCOME TAXES. The Fund's policy is to
                             comply with the requirements of the Internal
                             Revenue Code, as amended, which are applicable to
                             regulated investment companies and to distribute
                             all of its taxable income to its shareholders.
                             Accordingly, the Fund paid no federal income taxes
                             and no federal income tax provision was required.

                             At November 30, 1999, the Fund had a net tax basis
                             capital loss carryforward of approximately
                             $6,077,000, which may be applied against any
                             realized net taxable capital gains of each
                             succeeding year until fully utilized or until
                             November 30, 2002 ($293,000), November 30, 2003
                             ($5,154,000), and November 30, 2006 ($630,000) the
                             expiration dates.

                             DISTRIBUTION OF INCOME AND GAINS. Distributions of
                             net investment income, if any, are made monthly.
                             Net realized gains from investment transactions, in
                             excess of available capital loss carryforwards,
                             would be taxable to the Fund if not distributed,
                             and, therefore, will be distributed to shareholders
                             at least annually.

                             The timing and characterization of certain income
                             and capital gains distributions are determined
                             annually in accordance with federal tax regulations
                             which may differ from generally accepted accounting
                             principles. As a result, net investment income
                             (loss) and net realized gain (loss) on investment
                             transactions for a reporting period may differ
                             significantly from distributions during such
                             period. Accordingly, the Fund may periodically make
                             reclassifications among certain of its capital
                             accounts without impacting the net asset value of
                             the Fund.

                             STATEMENT OF CASH FLOWS. Information of financial
                             transactions which have been settled through the
                             receipt and disbursement of cash is presented in
                             the Statement of Cash Flows. The cash amount shown
                             in the statement of cash flows is the amount
                             reported as cash in the Fund's Statement of Assets
                             and Liabilities and represents the cash position in
                             its custodian bank at May 31, 2000. Significant
                             non-cash activity from market discount accretion
                             has been excluded from the Statement of Cash Flows.

                             INVESTMENT TRANSACTIONS AND INVESTMENT
                             INCOME. Investment transactions are accounted for
                             on the trade date. Interest income is recorded on
                             the accrual basis. Realized gains and losses from
                             investment transactions are recorded on an
                             identified cost basis. All discounts are accreted
                             for both tax and financial reporting purposes.

--------------------------------------------------------------------------------

2    PURCHASES AND SALES
     OF SECURITIES           For the six months ended May 31, 2000, investment
                             transactions (excluding short-term instruments) are
                             as follows:

                             Purchases                               $ 3,590,713

                             Proceeds from sales                       5,572,367

                                                                              19
<PAGE>   20

NOTES TO FINANCIAL STATEMENTS

--------------------------------------------------------------------------------

3    TRANSACTIONS WITH
     AFFILIATES              MANAGEMENT AGREEMENT. The Fund has a management
                             agreement with Scudder Kemper Investments, Inc.
                             (Scudder Kemper) and pays a monthly investment
                             management fee of 1/12 of the annual rate of .85%
                             of average weekly net assets. The Fund incurred a
                             management fee of $192,208 for the six months ended
                             May 31, 2000.

                             SHAREHOLDER SERVICES AGREEMENT. Pursuant to a
                             services agreement with the Fund's transfer agent,
                             Kemper Service Company (KSvC) is the shareholder
                             service agent of the Fund. Under the agreement,
                             KSvC received shareholder services fees of $12,000
                             for the six months ended May 31, 2000.

                             OFFICERS AND TRUSTEES. Certain officers or trustees
                             of the Fund are also officers or directors of
                             Scudder Kemper. For the six months ended May 31,
                             2000, the Fund made no direct payments to its
                             officers and incurred trustees fees of $6,222 to
                             independent trustees.

--------------------------------------------------------------------------------

4    REVERSE REPURCHASE
     AGREEMENTS              The Fund has entered into reverse repurchase
                             agreements with third parties involving its
                             holdings in U.S. Government Agency securities. At
                             May 31, 2000, the Fund had outstanding reverse
                             repurchase agreements as follows:

<TABLE>
<CAPTION>
                                                                      VALUE OF ASSETS SOLD                       WEIGHTED
                                                                        UNDER AGREEMENT         REPURCHASE       AVERAGE
                                       COUNTERPARTY                      TO REPURCHASE           LIABILITY       MATURITY
                                       ------------                   --------------------      -----------      --------
                                       <S>                            <C>                       <C>              <C>
                                       Merrill Lynch & Co.                $ 1,463,940           $ 1,457,000      128 days
                                       Salomon Smith
                                         Barney                            12,302,151            11,861,000       61 days
                                                                          -----------           -----------
                                                                          $13,766,091           $13,318,000
                                                                          ===========           ===========
</TABLE>

--------------------------------------------------------------------------------

5    EXPENSE OFF-SET
     ARRANGEMENTS            The Fund has entered into arrangements with its
                             custodian and transfer agent whereby credits
                             realized as a result of uninvested cash balances
                             were used to reduce a portion of the Fund's
                             expenses. During the six months ended May 31, 2000,
                             the Fund's custodian and transfer agent fees were
                             reduced by $1,629 and $536, respectively, under
                             these arrangements.

--------------------------------------------------------------------------------

6    LINE OF CREDIT          The Fund and several Kemper funds (the
                             "Participants") share in a $750 million revolving
                             credit facility for temporary or emergency
                             purposes. The Participants are charged an annual
                             commitment fee which is allocated pro rata among
                             each of the Participants. Interest is calculated
                             based on the market rate at the date of the
                             borrowing. The Fund may borrow up to a maximum of
                             33 percent of its net assets under the agreement.

 20
<PAGE>   21

SHAREHOLDERS' MEETING

ANNUAL SHAREHOLDERS' MEETING

An annual shareholders' meeting was held on May 25, 2000, for Kemper Strategic
Income Trust. Shareholders were asked to vote on two separate issues: election
of members to the Board of Trustees, and ratification of Ernst & Young LLP as
independent auditors. The following are the results for each issue:

1) Election of Trustees

<TABLE>
<CAPTION>
                                    For       Withheld
      <S>                        <C>          <C>
      James E. Akins             3,281,455     62,129
      Linda C. Coughlin          3,279,725     63,859
      James R. Edgar             3,285,033     58,551
      Arthur R. Gottschalk       3,286,133     57,451
      Frederick T. Kelsey        3,284,880     58,604
      Thomas W. Littauer         3,286,922     56,662
      Fred B. Renwick            3,281,018     62,566
      John G. Weithers           3,288,827     54,757
</TABLE>

2) Ratification of the selection of Ernst & Young LLP as independent auditors
   for the fund. This item was approved.

<TABLE>
<CAPTION>
         For     Against   Abstain
      <S>        <C>       <C>
      3,315,365   5,063     23,157
</TABLE>

                                                                              21
<PAGE>   22

NOTES

 22
<PAGE>   23

NOTES

                                                                              23
<PAGE>   24
TRUSTEES&OFFICERS
<TABLE>
<S>                               <C>                               <C>
TRUSTEES                          OFFICERS

JAMES E. AKINS                    MARK S. CASADY                    MAUREEN E. KANE
Trustee                           President                         Assistant Secretary
LINDA C. COUGHLIN                 PHILIP J. COLLORA                 CAROLINE PEARSON
Trustee                           Vice President and                Assistant Secretary
                                  Secretary
JAMES R. EDGAR                                                      BRENDA LYONS
Trustee                           JOHN R. HEBBLE                    Assistant Treasurer
                                  Treasurer
ARTHUR R. GOTTSCHALK
Trustee                           J. PATRICK BEIMFORD, JR.
                                  Vice President
FREDERICK T. KELSEY
Trustee                           ANN M. MCCREARY
                                  Vice President
THOMAS W. LITTAUER
Trustee and Vice President        KATHRYN L. QUIRK
                                  Vice President
FRED B. RENWICK
Trustee                           LINDA J. WONDRACK
                                  Vice President
JOHN G. WEITHERS
Trustee
</TABLE>

<TABLE>
<S>                                   <C>
 .............................................................................................
LEGAL COUNSEL                         VEDDER, PRICE, KAUFMAN & KAMMHOLZ
                                      222 North LaSalle Street
                                      Chicago, IL 60601
 .............................................................................................
SHAREHOLDER                           KEMPER SERVICE COMPANY
SERVICE AGENT                         P.O. Box 219066
                                      Kansas City, MO 64121-6066
 .............................................................................................
CUSTODIAN                             STATE STREET BANK AND TRUST COMPANY
                                      225 Franklin Street
                                      Boston, MA 02110
 .............................................................................................
TRANSFER AGENT                        INVESTORS FIDUCIARY TRUST COMPANY
                                      801 Pennsylvania Avenue
                                      Kansas City, MO 64105
 .............................................................................................
INDEPENDENT                           ERNST & YOUNG LLP
AUDITORS                              233 South Wacker Drive
                                      Chicago, IL 60606
</TABLE>



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