GpgOL Test Plan

Status: in progress

Contents

GpgOL Test Plan

Introduction

The purpose of this test plan is to ensure GpgOL works well on all supported Microsoft Windows operating systems with all supported versions of Microsoft Outlook.

Test environment

Choose one combination of the following target platforms supported by GpgOL.

Microsoft Outlook:

2003 (32bit)
2007 (32bit)
2010 (32 or 64bit)
2013 (32 or 64bit)
2016 (32 or 64bit)

Operation system:

Windows Vista (32 or 64bit)
Windows 7 (32 or 64bit)
Windows 8 (32 or 64bit)
Windows 10 (32 or 64bit)

For interoperability tests additional mail clients will be tested together with Outlook/GpgOL:

Thunderbird with Enigmail-Add-On (on Windows, MacOS or GNU/Linux)
Apple Mail with GPGTools (on MacOS)
Kontact Mail (KMail) enterprise 35 (on GNU/Linux)
Kontact Mail (KMail) of KDE 4.14 (on GNU/Linux)

It is recommended to use a clean virtual test environment, e.g. with VirtualBox.

Preconditions

email account A on IMAP/SMTP server
email account B on Exchange Server 2013 or later
OpenPGP public key (*.asc or *.gpg) and private key (*.asc or *.gpg)
S/MIME certificate chain (*.pem) and private key (*.p12)

Tests

Testsuite 1: GpgOL basic crypto tests

Send crypto mails from/to same Outlook account.

1.1 PGP/MIME

Send mails with PGP/MIME:
a) sign and verify
b) encrypt and decrypt
c) sign/encrypt (with attachment*) and decrypt/verify (and check attachment)

1.2 S/MIME

Send mails with S/MIME:
a) sign and verify
b) encrypt and decrypt
c) sign/encrypt (with attachment*) and decrypt/verify (and check attachment)

(*) Attachment should contain umlauts in filename (e.g. fooäüö.txt)

Testsuite 2: GpgOL extended tests

2.1 Exchange Server

Run all tests from testsuite 1 via Exchange Server.

2.2 Move mails

Move some encrypted mails from inbox into an other folder. Check with an other IMAP client that all mails are always encrypted.

2.3 Drafts

Create new message. Mark message with "sign" and "encrypt". Close and save mail as draft. Open draft again. Check if the message is still marked with "sign" and "encrypt".

2.4 Cancel crypto operation

Create a mew message. Mark as sign/encrypt. Click send. Cancel certificate selection dialog. Check if the message is not sent.

2.5 Sent messages

Send a signed/encrypted message. Check the sent folder ("Sent messages") if the mail is still signed/encrypted.

2.6 Reply

Reply to an encrypted mail. Check if the quoted text contains the decrypted message.

2.7 Disable GpgOL

Disable the GpgOL plugin in Outlook (via COM add-ons). Select a OpenPGP signed/encrypted mail. Check that the mail cannot decrypt/verify.

2.8 Deactivate GpgOL's S/MIME (GpgSM)

Open a a S/MIME sign/encrypted mail (which was signed/encrypted with GpgOL). Deactivate S/MIME in GpgOL's option dialog. Close and reopen the mail. Check that Outlook's S/MIME implementation can decrypt/verify this mail.

2.9 Close Outlook

Open a signed/encrypted mail. Close Outlook. Answer "Yes" if Outlook wants to save the changes. Restart Outlook.

Check with an other mail client (via IMAP) before and after restart of Outlook that the mail is never unencrypted on server.

2.10 Unknown recipient

Try to encrypt a message to a unknown email address. Check that Kleopatra cannot match a suitable certificate.

2.11 Cannot decrypt

Send an encrypted email to yourself but select an other certificate for encryption (not the own certificate). Check that GpgOL cannot decrypt the received message.

2.12 Cannot sign

Remove your certificate (incl. secret key). Try to sign a new message. Check that GpgOL cannot sign the message.

2.13 Cannot encrypt

Remove your certificate (if still available). Try to encrypt a new message to yourself. Check that GpgOL cannot encrypt the message.

2.14 Signature with wrong address

Create or import new secret key which does not match to Outlooks email address. Send a signed mail to yourself but select the new certificate for signing. Verify the signature. Check the warning that the email address not contained in the certificate.

Testsuite 3: Interoperability tests (Outlook's built-in S/MIME)

3.1 Receive S/MIME mails with GpgOL

Send S/MIME crypto mails from Outlook (with it's built-in S/MIME implementation) to an other Outlook (with GpgOL).

a) sign and verify
b) encrypt and decrypt
c) sign/encrypt (with attachment*) and decrypt/verify (and check attachment)

3.1 Send S/MIME mails with GpgOL

Send S/MIME crypto mails from Outlook (with GpgOL) to an other Outlook (with it's built-in S/MIME implementation).

a) sign and verify
b) encrypt and decrypt
c) sign/encrypt (with attachment*) and decrypt/verify (and check attachment)

Testsuite 4: Interoperability tests (Kontact Mail)

Send crypto mails between Kontact Mail (KMail) and Outlook (with GpgOL).

4.1 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)

4.2 S/MIME

4.3 INLINE/PGP

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

Testsuite 5: Interoperability tests (Thunderbird)

Send crypto mails between Thunderbird (with Enigmail) and Outlook (with GpgOL).

5.1 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)

5.2 S/MIME (with Thunderbird's S/MIME implementation)

5.3 INLINE/PGP

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

Testsuite 6: Interoperability tests (GPGTools)

Send crypto mails between Apple Mail (with GPG for Mail plugin from GPGTools) and Outlook (with GpgOL).

6.1 PGP/MIME

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

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