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Is it possible to raise this ridiculously low limit?
Bash gives me a much higher and more useful limit.

$ getconf ARG_MAX
2097152

I guess it would be pretty hard to shorten the proguard command. When new modules are added it even grows bigger.
It is probably best to add a Quirks section to the INSTALL file and provide a Windows workaround to raise the command size.

I don't see a way to raise the limit. Microsoft gives Information and suggests solutions under http://support.microsoft.com/kb/830473, but i think none of the solutions are usable here.

The Plugin uses com.jayway.maven.plugins.android.CommandExecutor (the default implementation which is also in this file). The command is then executed via org.codehaus.plexus.util.cli.CommandLine which in fact uses cmd.exe to run the command.

• Use proguard-maven-plugin (https://github.com/wvengen/proguard-maven-plugin) directly. This plugin uses ant (see https://github.com/wvengen/proguard-maven-plugin/blob/master/src/main/java/com/github/wvengen/maven/proguard/ProGuardMojo.java) to execute proguard and maybe the problem does not exist there.
• Supply a patch for the android-maven-plugin where the executor uses the Runtime.exec call from Java directly to run proguard instead of wrapping it into cmd.exe.
• Disable Proguard runs on Windows and add a note to the INSTALL file.

The first one is of course preferable, because it does not involve patching plugins.
Proguard is optional and only enabled in the release profile. So option 3 is ok for me, too.