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Thank you for this feedback. The team may reach out for more information on triaging or reproducing this issue.

I have tried the example project you've provided, it does not reproduce.

Could you please try running with -Pandroid.useDexArchive=false? This disables the new dexing pipeline, and fallbacks to the old one.

@Mario Did you get a chance to try the build with -Pandroid.useDexArchive=false flag?

I'm the college of @Mario and I make it work without issues and without using  -Pandroid.useDexArchive=false by using alpha6 and removing retrolambda

Sorry my comment from Apr 21, 2017 12:41PM was wrong.
With -Pandroid.useDexArchive=false it looks like this

:app:transformClassesWithDesugarForNonpayItalyCompatDebugAndroidTest
:app:transformClassesWithPreDexForNonpayItalyCompatDebugAndroidTest
Dex: warning: Ignoring InnerClasses attribute for an anonymous inner class
(org.ccil.cowan.tagsoup.Parser$1) that doesn't come with an
associated EnclosingMethod attribute. This class was probably produced by a
compiler that did not target the modern .class file format. The recommended
solution is to recompile the class from source, using an up-to-date compiler
and without specifying any "-target" type options. The consequence of ignoring
this warning is that reflective operations on this class will incorrectly
indicate that it is *not* an inner class.

:app:transformDexWithDexForNonpayItalyCompatDebugAndroidTest FAILED

FAILURE: Build failed with an exception.

* What went wrong:
Execution failed for task ':app:transformDexWithDexForNonpayItalyCompatDebugAndroidTest'.
> com.android.build.api.transform.TransformException: com.android.ide.common.process.ProcessException: java.util.concurrent.ExecutionException: com.android.dex.DexIndexOverflowException: method ID not in [0, 0xffff]: 65536

We updated our example repo https://github.com/originx/Gradle_troubles_android_enteprise where you can see the issue.
Just run

./gradlew spoonGermanyDebugAndroidTest
or
./gradlew spoonGermanyDebugAndroidTest -Pandroid.useDexArchive=false

and you will see the issue

Your tests do not fit into a single dex file. I've tried plugin 2.3.0 (I've also had to enable retrolambda for app, core, and pay modules), and the number of references that are generated is higher than 64k.
Please note that if you are using plugin's internal or Retrolamba support for Java 8 language features, for each lambda expression you will generate 3 additional references, so it might affect your reference count quite significantly.

Hello and thank you for the reply. What is the expected fix for this the ticket status was moved to "verified (fixed)" it is rather confusing for me. Do you suggest we have too many tests and that's it?
Could you please clarify?
Thank you for your time

Your test sources and test-only dependencies are generating too many references. Java 8 language features are not related to this, as even when I remove compileOptions from all modules, the test dependencies cannot fit into a single dex file.

I suggest you take a look at Proguard rules that you can specify when running the tests - https://google.github.io/android-gradle-dsl/current/com.android.build.gradle.internal.dsl.ProductFlavor.html#com.android.build.gradle.internal.dsl.ProductFlavor:testProguardFile(java.lang.Object). I've also updated the bug status, not to be confusing.

Hello,

Thank you for the link and clarification.
Pardon my many questions I just want to understand the problem better.

We use proguard for the app and define proguard rules which classes to keep for the test runner that we need early on in the start of the test run.
Why did it work with older build tools?
Also why doesnt multidex work for the test app or proguard rules from the debug builds?

Thank you for the quick response

No worries Mario, I would also like to understand where the issue is coming from :)

The fact that it worked with 2.3.0 and not with 2.4.0-alpha4 is worrying. Because I am unable to reproduce with the test project you've provided, can you please compare the contents of build/intermediates/transforms/preDex/androidTest/ when building tests:
- from clean, with 2.3.0
- from clean, with 2.4.0-alpha4, with -Pandroid.useDexArchive=false
The content of these 2 directories should be the same. Please report any differences.

The support in the test runner is missing to be able to run test apk with multiple DEX files. I don't have much more info on it, sorry.

Hello,

sorry I am  a bit restricted in the work environment so I cannot build the demo project from this location but I executed a diff on a real project where the issue happens for dex folders (predex is not available in 2.3.0) its disabled for our project.

this is for 2.3.0 and 2.4.0-alpha4 in location build/intermediates/transforms/dex/androidTest/nonPayMexicoBleeding for following command:
./gradlew clean connectedNonpayMexicoBleedingDebugAndroidTest
I used flag -Pandroid.useDexArchive=false for 2.4.0 only.

diff -rq nonpayMexicoBleeding\ 2.3.0/ nonpayMexicoBleeding\ 2.4.0-alpha4/
Result:
Only in nonpayMexicoBleeding 2.3.0/debug/folders/1000: 1
Only in nonpayMexicoBleeding 2.3.0/debug/folders/1000: 10
Only in nonpayMexicoBleeding 2.4.0-alpha4/debug/folders/1000: 1f

Does this help?