GpgOL test plan

Here you can find information about the manual testing progress of GpgOL.

What should be tested?

We want to ensure GpgOL works well on all supported Microsoft Windows operating systems with all supported versions of Microsoft Outlook.

The tests refer to the signing and encrypting process in Microsoft Outlook using GpgOL, the transmission of encrypted and/or signed emails, and the receiving of encrypted and/or signed emails.

The tests are not only performed with messages from and to Microsoft Outlook, but also with other Windows and Linux mail clients which are supported by GnuPG, especially:

• Microsoft Outlook 2010 32bit (on Windows 7 64bit)
• Microsoft Outlook 2013 64bit (on Windows 8 64bit)
• Microsoft Outlook 2016 32bit (on Windows 7 32bit)
• Microsoft Outlook 2016 64bit (on Windows 8 64bit)
• Microsoft Outlook 2016 64bit (on Windows 10 64bit)
• Thunderbird with Enigmail-Add-On (on Windows or GNU/Linux)
• KMail of Kontact enterprise 35 (on GNU/Linux)

The tests will refer to the usage of PGP/MIME and PGP/Inline.

To test out the different versions of Microsoft Outlook on different platforms and CPU-Architectures a virtual test environment was recommenended, e.g. VirtualBox.

Test plan

Check if GpgOL can perform the following test suites without errors.

1. Outlook <--> Outlook

Send crypto emails between Outlook (GpgOL) and Outlook (GpgOL).

1.1 Using PGP/MIME

a) sign -> verify
b) encrypt -> decrypt
c) sign/encrypt with attachment -> decrypt/verify and check attachment

1.2 Using S/MIME

a) sign -> verify
b) encrypt -> decrypt
c) sign/encrypt with attachment -> decrypt/verify and check attachment

2. KMail <--> Outlook

Send crypto emails between KMail and Outlook (GpgOL).

2.1 Using PGP/MIME

a) sign (KMail) -> verify (GpgOL)
b) encrypt (KMail) -> decrypt (GpgOL)
c) sign/encrypt with attachment (KMail) -> decrypt/verify and check attachment (GpgOL)
d) answer to (a): sign (GpgOL) -> verify (KMail)
e) answer to (b): encrypt (GpgOL) -> decrypt (KMail)
f) answer to (c): sign/encrypt with attachment (GpgOL) -> decrypt/verify and check attachment (KMail)

2.2 Using S/MIME

a) sign (KMail) -> verify (GpgOL)
b) encrypt (KMail) -> decrypt (GpgOL)
c) sign/encrypt with attachment (KMail) -> decrypt/verify and check attachment (GpgOL)
d) answer to (a): sign (GpgOL) -> verify (KMail)
e) answer to (b): encrypt (GpgOL) -> decrypt (KMail)
f) answer to (c): sign/encrypt with attachment (GpgOL) -> decrypt/verify and check attachment (KMail)

2.3 Using PGP/Inline

a) sign (KMail) -> verify (GpgOL)
b) encrypt (KMail) -> decrypt (GpgOL)
c) sign/encrypt without attachment (KMail) -> decrypt/verify (GpgOL)

3. Thunderbird <--> Outlook

Send crypto emails between Thunderbird (Enigmail) and Outlook (GpgOL).

3.1 Using PGP/MIME

a) sign (TB) -> verify (GpgOL)
b) encrypt (TB) -> decrypt (GpgOL)
c) sign/encrypt with attachment (TB) -> decrypt/verify and check attachment (GpgOL)
d) answer to (a): sign (GpgOL) -> verify (TB)
e) answer to (b): encrypt (GpgOL) -> decrypt (TB)
f) answer to (c): sign/encrypt with attachment (GpgOL) -> decrypt/verify and check attachment (TB)

3.2 Using S/MIME (with Thunderbird's S/MIME implementation)

a) sign (TB) -> verify (GpgOL)
b) encrypt (TB) -> decrypt (GpgOL)
c) sign/encrypt with attachment (TB) -> decrypt/verify and check attachment (GpgOL)
d) answer to (a): sign (GpgOL) -> verify (TB)
e) answer to (b): encrypt (GpgOL) -> decrypt (TB)
f) answer to (c): sign/encrypt with attachment (GpgOL) -> decrypt/verify and check attachment (TB)

3.3 Using PGP/Inline

a) sign (TB) -> verify (GpgOL)
b) encrypt (TB) -> decrypt (GpgOL)
c) sign/encrypt with attachment (TB) -> decrypt/verify and check attachment (GpgOL)

Test Results

The detailed description of how the test was performed, what kind of results were expected and what the actual result was like.

1.1.a Using PGP/MIME

Windows 7 32 Outlook 2016

Using Gpg4Win version 2.2.6 and gpgol.dll beta 1.3.0-beta85 (2015-11-04). Imported two necessary certificates in Kleopatra and authenticated them manually.

Signing an E-Mail with OpenPGP and sending it worked without a noticeable problem.

Receiving an signed E-Mail and read it worked without a problem.

To verify the received E-Mail, it was necessary to open it (The E-Mail) in an external window (double click) and navigate to the GpgOL-tab afterwards, which is inconvenient. It was not possible to verify the E-Mail inside the Outlook-Main-Window (missing option).

Expected:

• The E-Mail may be verified automatically
• The E-Mail may be verified from inside the main window (GpgOL-tab)

Result:

• Successful verification from an external window

1.2.a Using S/MIME

Windows 7 32 Outlook 2016

Using Gpg4Win version 2.2.6 and gpgol.dll beta 1.3.0-beta85 (2015-11-04). Imported two necessary certificates in Kleopatra and authenticated them manually.

(like in 1.1.a) Signing an E-mail with S/MIME and sending it worked without a noticeable problem.

Receiving a signed E-Mail and reading it worked without a noticeable problem.

The process of verifying failed. The error message was "Decryption failed: no data" (sic: (German) "Entschlüsseln fehlgeschlagen: Keine Daten.") The detailed error decryption was "input error: unknown error" (sic: (German) "Eingabefehler: Unbekannter fehler").

Expected:

• The E-Mail may be verified successful.
• The E-Mail may be verified from inside the main window (GpgOL-tab)

Result:

• The verification failed. Error message: "Decryption failed: no data" | "input error: unknown error"

Test matrix

Legend:
? = untested
x = passed
F = failed

+++ Tested GpgOL version: X.X.X +++

¹) To verify and decrypt an email, it is necessary to open it in an external window, which is inconvenient.