When the "Restore Open Asset Tabs on Restart" option is turned on in the Editor Preferences window, closing the Editor while a debugger is attached appears to remove any saved asset tabs from the EditorPerProjectUserSettings.ini file. When this option is enabled, open asset tabs add an "OpenAssetsAtExit=/Path/To/Asset" entry to the EditorPerProjectUserSettings.ini file. All of these entries are deleted from the .ini file if the Editor is closed while a debugger is attached, even if asset windows are still open in the Editor when it is closed.
No. This same behavior was seen in 4.18.3.
The tabs that were previously open are not re-opened when the Editor starts.
The tabs that were previously open are re-opened when the Editor starts.
There's no existing public thread on this issue, so head over to Questions & Answers just mention UE-72962 in the post.