Workflow-triggered Plugin works if run on form, but not from home screen

I have an on demand workflow which changes a 2-option field, "trigger", to true or false.

I have a plugin on Update for the entity which checks the "trigger" field like this

if (entity.Contains("trigger") != true)
                return;

and then the Plugin updates the entity with new stuff. I have a context.Depth > 1 check to prevent loop.

This works as intended if I run the WF on the form of an account.

But when I try to run it from home/list screen (single or batch doesn't matter), it won't update.

I check the entity and see that the trigger has been thrown, but the plugin hasn't.

I've tried put the plugin on different settings, sync and async - nothing helps.

I've also tried changing the WF to immediate or background, nothing there either.