Test report for GpgOL 1.4.0-beta55 (2016-03-10)
Gpg4win-3.0.0-beta126 with Windows 10 64bit with Outlook 2016 64bit
Testsuite 1: GpgOL basic crypto tests
1.1 OpenPGP/MIME
Semi-OK
Signing an E-Mail crashed Outlook once in a while, it didn't seem to appear in a pattern, but when it happened, it was right after the dialogue with Kleopatra where it asks which certificate to use to send and which certificates to use as recipient.
I tried to send signed and encrypted messages. When Outlook didn't crash, signed messages were always send and displayed correctly, but encrypted messages weren't always correctly decrypted. Sometimes the mail was just empty and 2 attachments (dat and bin-file) were displayed on top.
Also, the Sign an Encrypt Logos are only displayed, when the mail editing window is detached from the main Outlook window. When you use the reply or forwarding button, the standard in-Outlook-View appears and there is no encrypt or sign option there.
1.2 S/MIME
OK
Importing the correct certificates into Outlook ain't very nice. I had several problems verifying the correctness of the created S/MIME certificates. Even though I imported the complete trust-chain the certificate wasn't trusted. I used the Windows Certificate Manager to explicit trust this very certificate.
After I managed the registration of the certificates in Outlook i could send and receive S/MIME encrypted and signed messages.
Testsuite 2: GpgOL extended tests
2.1 Exchange Server
Semi OK
Tried with Active Sync, worked as described in 1.1.
2.2 Move mails
OK
2.3 Drafts
OK
2.4 Cancel crypto operation
OK
2.5 Sent messages
Semi-OK
Worked as described in 1.1
2.6 Reply
Semi-OK
Worked as described in 1.1
2.7 Disable GpgOL
OK
2.8 Deactivate GpgOL's S/MIME (GpgSM)
N/A
Used the Outlook built-in SMIME
2.9 Close Outlook
OK
2.10 Unknown recipient
OK
2.11 Cannot decrypt
2.12 Cannot sign
2.13 Cannot encrypt
2.14 Signature with wrong address
2.15 Attachments
Semi-OK
Worked as described in 1.1
2.16 Forward / reply to encrypted mail
OK but not user-friendly (as described in 1.1)
2.17 Office elements
OK but not user-friendly (as described in 1.1)
2.18 Inline editors
OK but not user-friendly (as described in 1.1)
2.19 Address book recipient
OK
2.20 Shared folders
2.21 Kleopatra startup
OK
Testsuite 6: Interoperability tests (GPGTools)
6.1 OpenPGP/MIME
Signature send from the Mac to Windows weren't displayed correctly the other way worked good. Encrypt only and encrypt and sign worked correctly in both ways.
6.2 S/MIME
The Mailprogram used on the Mac didn't support SMIME