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Hey @heyquentin did you ever get this figured out? I opened PR mitre/builder#23 that resolves the chunked issues with Docker-Py. However, I cannot seem to get a payload generating dynamically with the builder plugin based on the example here (https://caldera.readthedocs.io/en/latest/Dynamically-Compiled-Payloads.html#basic-example) or yours. Any further luck debugging this?

Do you have this specific version of the requests module: (pip install requests==2.29.0). I'm running Caldera in a virtual environment which I think is nice for stuff like this. This is what I have in my notes for setup. I've used these notes to setup Caldera on a few machines and I think they should be good to go. See if there's any differences between your env:

Install unzip, Go, pip3, venv
$ sudo apt update
Go: https://go.dev/doc/install
$ sudo apt install unzip p7zip-full7za python3.8-venv python3-pip

Create a new venv
$ unzip caldera.zip
$ cd caldera/plugins/builder, run ./install.sh to install Docker for the Builder plugin
$ cd ../../
$ rm -rf calderaEnv
$ python3 -m venv calderaENV
$ source calderaENV/bin/activate

Install requirements
$ pip3 install -r requirements.txt
$ pip3 install requests==2.29.0
$ pip3 install pyminizip

Run the server.
$ python3 server.py -E config --log DEBUG

I also made notes specifically on this problem (I take notes on everything that takes me more than 30 seconds to fix lol) See if these help you:

DO NOT install docker-py

I was trying to use dynamically compiled executables but the builder plugin wouldn't start. I tracked down the problem to the requests module: #2793

To fix this just install requests 2.29 in your python env
$ pip install requests==2.29.0

If you get this error:
2023-07-26 10:52:40 - ERROR (c_plugin.py:70 enable) Error enabling plugin=builder, module 'docker' has no attribute 'from_env'
Install Docker from the requirements.txt. You probably nave a newer docker installed

This FileNotFoundError error:
2023-08-23 23:31:41 - ERROR (c_plugin.py:70 enable) Error enabling plugin=builder, ('Connection aborted.', FileNotFoundError(2, 'No such file or directory'))
Go into plugins/builder and run ./install.sh

Thanks for the quick reply! Interesting you mention using requests here. I was able to resolve the issue of builder not starting by upgrading docker-py and did not have to touch requests. But I think both are "fixes" to the problem. Ultimately we are running into a dependency issue that will need to get resolved. Either the urllib/requests needs to be sorted out or docker-py needs to be bumped to accommodate the issue.

Anyway, getting the builder plugin enabled was not my issue. My issue was trying to figure out why the payload was not generating. I realized after following the code that the actual payload generation is not triggered unless and until the ability is linked in an actual operation under the planning service (