Unable to categorize or follow-up an encrypted eMail

=================== ENGLISH: ===================


I’m using Outlook 2016 with GpgOL 2.4.2 and Exchange 2013.
I have found out that the following options are not working in Outlook if applied to encrypted eMails:

E-Mail → Right mouse click → Categorize → …
E-Mail → Follow up → …

For example, when selecting “Categorize…->Red category” for an encrypted eMail, then a red line appears in the detail view
and you may think it is OK. But nothing changes in the list view. Than, when switching to another eMail and than back to the just
categorized eMail, then the red line does not appear anymore und also no error message appears.

But it works with unencrypted eMails.

Is anything wrong with my setup/configuration or is it a known issue, can you test whether it works for you?

Thank you.

=================== GERMAN: ===================

Guten Tag,

ich verwende Outlook 2016 mit GpgOL 2.4.2 und Exchange 2013.
Ich habe festgestellt, dass folgende Funktionen in Outlook bei verschlüsselten E-Mails nicht funktionieren:

E-Mail → Rechtsklick → Kategorisieren → …
E-Mail → Zur Nachverfolgung → …

Wenn man z.B. bei einer verschlüsselten E-Mail “Kategorisieren->Rote Kategorie” auswählt, dann erscheint in der Detailansicht ein Roter Balken und man denkt es ist OK.
Allerdings ändert sich nichts in der Listenansicht. Wenn man dann eine andere E-Mail anklickt, und dann wieder die eben “kategoriesierte” E-Mail,
dann ist der vorher angezeigte rote Balken auch weg und es gibt keine Fehlermeldung.

Aber mit unverschüsselten E-Mails funktioniert es.

Stimmt etwas nicht mit einer Installation/Konfiguration oder ist das ein bekanntes Problem, könnt ihr kurz selbst testen?

Vielen Dank.


Me too. Win10pro Outlook 2013 64 bit GpgOL 2.4.2. I can add a category but isn’t shown in the msg line nor able to add using the column of categories.

Josep M.

No categorize.png

Same here. Is there any workaround known?


the workaround is to add the catgeory / flag while the mail is not opened and decrypted. For example if you right click on it while you have another mail open.

Best Regards,


I know this trick, but this does not work in the newest Outlook / Gpg4win Version anymore.

I agree too rebuh! It fails in any msg with the blue icon on the msgs list. Doesn’t mather if you do it with or w/o msg selected. Outlook 2013 64 bit win 10 pro.

Josep M.

can you say with which version it stopped working?


Unfortunately not, but I think it was an update on outlook side (I don’t regularly update gpg4win and outlook installs all updates automatically).

which version of Outlook are you running now?
Do you remember which one you may have had before?

SMTP transport or Exchange?


Fails on both types. I’m receiving MS security notifications on a pop3 and on a outlook.com accounts. Both fail. Msgs are signed not encrypted (blue icon on the left inthe msgs list). MS some times fais to sign msgs well, and some times it signes fine. Both fail to categorize. And blue icon appears on both msgs well or bad signed but not always. Outlook 2013 64 bit.
I can try to retrofit to old versions… Where are they located to download?



which version of Outlook are you running now?

Office 365, newest Outlook versio (16.0.12430.20112, 32-bit).

Do you remember which one you may have had before?

No, the versions are changing permanently.

SMTP transport or Exchange?


Another curious behaviour: When I receive an e-mail from Microsoft it is classified as trust level 3. When i change to view another msg and come back it is classified as a trust level 4.

Rebuh, Josep,
thanks for adding more details.

I’ll guess we’ll have to inquire, if we have an idea, (probably when Andre gets around taking a look.).

Just wondering: Are we talking S/MIME or OpenPGP/MIME mails or both?
(This would make a difference with the trust-level, but also for other things.)


In the header of the email, I see:

Content-Type: multipart/signed; micalg=pgp-sha512;

That means OpenPGP/MIME, right?

Is there a more convenient way of determing which encryption is used?

Yes, this is OpenPGP/MIME.

You should be able to see this in the upper part in the blue box
when opening an emal


I’m only using Gpg4win for openPGP, otherwise I’m using Outlook native support for S/MIME. And the msgs coming from Microsoft are in-line signed no MIME.

as for the trust level question, it is better to open a new discussion thread
I think. :slight_smile:



just to say: I can reproduce the issue. But I’ll have to stare down the logs a bit to understand why the old workaround does not work anymore. It seems that Outlook keeps references to the decrypted mails around longer then it did in the past. Probably some kind of optimization in the Outlook Object Model that is problematic for us.

I still have ideas about making the flag changes possible even when the mail is visible I think I should rather focus my time on that, as this would also solve the issue when a mail is unopened. But it’s very fagile as we basically have to reconstruct the original mail using MAPI.

Best Regards,