Hello, I have the same issue.
Coud this issue be related to this bug ? https://github.com/FreeRDP/Remmina/commit/5b172d76fc79e328c0ca6ce6fcddba777da8f11c Fix seems trivial, but author says it fixes issues #556 (clipboard not synchonizing between RDP sessions and host) and #583 (Clipboard + Windows 2008 Server R2 SP1 + Google Chrome). There is another fix that could be also interesting : https://github.com/FreeRDP/Remmina/commit/d3dd62a6a9edfa6117ac85159a9224d3ed655eaf Seems to explicitly set the sync member of a newly allocated structure, this could explain the randomness nature of the issue. Regards, Fred