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I was installing Yowsup to see If could run some tests. During the process threw an error that mentioned that jpeg is not installed and that it could be disabled from the installation.
Did you install jpeg? Or, did you disable it on the installation? I mean, this might be a cause of issues when trying to send images.
I found Upload and send Media on the Yowup github. Is this what you are looking for? I suggest you to check it out.
Also, since this is a third party application, you'd probably get a more accurate answer regarding its operation with the original author. You can contact them in Issues · tgalal/yowsup.
I went through the links you suggested but I am unable to understand the yowsup architecture as I am new to it. I understand that I need to request a URL to upload my data and then further send the msg. For which I need to make some modifications to my Yowsup-cli library (correct me if wrong!!). But i am not very sure where to add my layer.py and stack.py files and how to execute them to enable my board sending msgs.
Unfortunately I'm not familiar with the library and as I explained above I couldn't install it due to an error about jpeg... so I was not able to test it. My best suggestion for you would be to contact the author of this library in the link I suggested before, they might help you with the architecture and the changes needed to use this library.