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Is there a way I can make DashOPro rename the classes differently, everytime I start an obfuscation run?

What I want is, that someone who knows an old obfuscated version of my application will not see the same names for the same classes in a new obfuscated version.

Thanks in advance.

There are a few things you can try.

First, are you familiar with Incremental Obfuscation?
When you obfuscate, DashO produces a file (project.map by default) that contains the renaming translation used. You could edit this map and use it as an input, though this could be tedious and potentially error prone.

You can set a class prefix to make things slightly different. Changing the prefix each release.

One technique that I am pulling off the top of my head but creating dummy classes that do nothing and are not used at all will 'push' the name up. Example,
if you had classes
class1 -> a
class2 -> b
class3 -> c
before, add in a couple dummy classes
class0_dummy -> a
class1 -> b
class1_dummy -> c
class2 -> d
class3 -> e

However, this would not affect the renaming of the methods internally.

Hope this helped.