Yes. But it seems to have resolved itself in the last few months. I'm using Molly I'm not sure if that matters

When the phone is cold. I have to unlock the work profile, then unlock signal/molly. If I am sharing to a contact from the share quick contacts list, it seems to always work the first time.

If I'm sharing to a contact that I have to open signal to select it used to work 50/50 the first time, but sharing the second time after unlocking everything worked.