Hi Cassy, 

Have you found a solution or a workaround? We have a different issue with reusable workflows conditional start, I'm currently looking for hints.

For your situation, a workaround could be to use the Filter action to stop unneeded processing of wrong content types as the first in the definition.

hi yes I had this back from support:

Our developers have come back to me with regards to this issue This issue is occurring due to the column name being above 32 characters long, the spaces add an additional 7 characters each. I have tested your solution with a shorter column name and I did not have any issues Can you test your solution with a shorter column name and let me know what happens

AND

This behavior is due to the limitations of SharePoint. Microsoft have imposed the 32 character limit on the internal column names which causes the behaviors that we observed. This is not something that we can change the workaround would be to have shorter column names instead of spaces "-,_" could be used.

I tested this and it worked...

Hi @cassymfreeman 

Hope you're keeping well. Wondered if I could drag this up as we have an issue with Site Collection Reusable Workflow Templates. We're publishing a workflow with a conditional start, but when we then associate it with the content type in the list, when published as a "Conditional" start the checkbox in the workflow settings are greyed out.

Just wondering if you also saw this and worked around it, or whether there's a new issue in SP2019 that we've hit.

Appreciate this is a few years old and might not be something to can check, but thought I'd ask.

Thanks

i think that is normal behaviour. If you just associate it in that way (with them greyed out) you should find the workflow starts when the conditions are met.

Hit me up for a call if you'd like, happy to take a look with you (be nice to catch up)