Updateable Dashboard fails to update sometimes

We have an updateable dashboard that occasionally fails to update the record. This dashboard is updating task status on a project, and changing the status on tasks of certain projects does not update. Row in dashboard does not turn red, and attempting to update from the BAQ returns no errors, the data just does not update.

At first I thought this might be BPM related, so I tried updating the status through Project Entry and it updates just fine without any errors.

Kind of stuck on this one since it does not happen all the time and there are no error messages to debug with.

Try turing on App Server Logging and see what you get.
If you wrote code, you can also add your own logging:
Ice.Diagnostics.Log.WriteEntry("");

App server logging is turned on and there are no errors there either.

So you are saying it simply does NOTHING?
Did you write the code or did it get generated for you? It seems very odd that it would do that (although not impossible).