The java 1.4 version of the jar command (both 32-bit and 64-bit) can not extract files that are larger than 2^31-1 (2147483647). However, it can add files that are larger than this. The result is that you can have an archive with files in it that can not be extracted without getting a ZipException like this:

java.util.zip.ZipException: invalid entry size (expected 2920611840 but got -1374355456 bytes)

This is a classic signed int overflow situation -- -1374355456 == unsigned 2920611840

java 1.5 and later does not have this problem

Here is a test case

+ /usr/sbin/mkfile -n 2147483648 2147483648
+ /usr/j2se/bin/java -version
java version "1.4.2_06"
Java(TM) 2 Runtime Environment, Standard Edition (build 1.4.2_06-b03)
Java HotSpot(TM) Client VM (build 1.4.2_06-b03, mixed mode)
+ /usr/j2se/bin/jar cvf test.jar 2147483648
added manifest
adding: 2147483648(in = -2147483648) (out= 2087262)(deflated 100%)
+ /usr/j2se/bin/jar tvf test.jar
     0 Thu Apr 27 13:01:34 PDT 2006 META-INF/
    71 Thu Apr 27 13:01:34 PDT 2006 META-INF/MANIFEST.MF
java.util.zip.ZipException: invalid entry size (expected 2147483648 but got -2147483648 bytes)
        at java.util.zip.ZipInputStream.readEnd(ZipInputStream.java:367)
        at java.util.zip.ZipInputStream.read(ZipInputStream.java:141)
        at java.util.zip.ZipInputStream.closeEntry(ZipInputStream.java:91)
        at sun.tools.jar.Main.list(Main.java:744)
        at sun.tools.jar.Main.run(Main.java:192)
        at sun.tools.jar.Main.main(Main.java:904)