= GpgOL Test Plan

**Status: in progress**

<<TableOfContents(3)>>

== 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 [[https://www.virtualbox.org/|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/~M~I~M~E 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 P~G~P/~M~I~M~E:\\
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/~M~I~M~E:\\
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 signed/encrypted mail. Check that the mail cannot decrypted/verify.


==== 2.8 Deactivate GpgOL's S/MIME (GpgSM)

TODO

=== Testsuite 3. Interoperability tests (Kontact Mail)

Send crypto mails from Kontact Mail (KMail) to Outlook (GpgOL). 

==== 3.1 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)

==== 3.2 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)

==== 3.3 Using no-mime-PGP
a) sign (KMail) -> verify (GpgOL)\\
b) encrypt (KMail) -> decrypt (GpgOL)\\
c) sign/encrypt without attachment (KMail) -> decrypt/verify (GpgOL)\\


=== Testsuite 4. Interoperability tests (Thunderbird)

Send crypto mails from Thunderbird (Enigmail) to Outlook (GpgOL). 

==== 4.1 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)

==== 4.2 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)

==== 4.3 Using no-mime-PGP
a) sign (TB) -> verify (GpgOL)\\
b) encrypt (TB) -> decrypt (GpgOL)\\
c) sign/encrypt with attachment (TB) -> decrypt/verify and check attachment (GpgOL)