FULL PRODUCT VERSION :
java version "1.5.0_05"
Java(TM) 2 Runtime Environment, Standard Edition (build 1.5.0_05-b05)
Java HotSpot(TM) Client VM (build 1.5.0_05-b05, mixed mode)

pack200 --version:
com.sun.java.util.jar.pack.Driver version 1.22, 04/05/05

ADDITIONAL OS VERSION INFORMATION :
Microsoft Windows 2000 [Version 5.00.2195]

A DESCRIPTION OF THE PROBLEM :
Pack200 doesn't work properly on some jar files, notably some run through an obfuscator. This obfuscated code is valid Java bytecode and runs on any JVM I've tested on, from 1.1 on handheld devices on up. The code also runs fine when run with the latest version of Java and the java -Xfuture flag which verifies bytecode.

I repeatedly tried both of the workarounds in bug 5078608, neither of which work on the obfuscated file, but do seem to work on the unobfuscated files.

The jar file I'm testing against is available at:
http://futureboy.us/frinkjar/frink.jar

After repacking, the jar file does not pass any verification steps.

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
pack200 --repack --segment-limit=-1 frink.jar

jarsigner -verify frink.jar
jarsigner: java.lang.SecurityException: SHA-1 digest error for frink/f/f.class

Attempting to sign the resultant jar file, or following workaround 2 from bug 507860 also fails similarly.

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
These procedures seem to work correctly if the bytecode is not obfuscated. The packing procedure should be expected work on files containing valid bytecode, or third-party obfuscated code.

ERROR MESSAGES/STACK TRACES THAT OCCUR :
jarsigner: java.lang.SecurityException: SHA-1 digest error for frink/f/f.class

REPRODUCIBILITY :
This bug can be reproduced always.