More GpgOL weirdness with Click-to-Run Outlook and Exchange Online


I just checked, the old MIME problem with Click-to-Run Outlook and Exchange Online is still there with Gpg4Win 3.1.7 and Outlook “1903 (Build 11425.20204 Click-to-Run)”.

However, while checking that, I noticed another thing too.

The GpgOL status fields in the header section of the Outlook message display pane that usually are colored, say, green and blue if everything’s fine… they occasionally display without colors. As in, just black text on a white field, black border.

Haven’t had this happen with the first PGP message selected yet, but when looking at several in sequence might get this on the second message… or fifth, or… and then the next one usually is properly colored again.

Only once so far did I get one of the fields colored and the other B&W, but that has happened too.

Now, this kind of symptom is where I start to get nervous about race conditions, array bounds misses, memory leaks and such. Not that Outlook ever was particularly safe about those…

The Black & White issue is indeed likely a race condition but a harmless one.

With the colors we do the following:

→ Do the catgeories exist? → Yes → Ok
→ No → Create them
→ Add the categories to the mail.

Then when the mail is closed:
→ Remove the categories from the mail.
→ Are other mails still using them? → No → Remove the categories
→ Yes → Keep the categories.

When a category is on a mail but it’s removed in the category manager it is black and white. There seems to be a problem when switching fast that the “Do the categories exist” and the “Remove the categories” can be messed up in their execution order. Or even that Outlook does not allow very quick remove / readd of categories.

(We have to remove the categories so aggressively to avoid spamming the category manager with categories like “Level 2 trust in “””)

IMO having them sometimes in black and white is better then to sometimes leave such a “Level x trust” category hanging around.