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Maniphest T3419

GpgOL 2.0.1 doesn't recognize plain PGP messages as encrypted
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Description

I've upgraded GPG4Win from 2.3.3 to version 3.0.0, running Outlook 2010 on Windows 7.
The new GpgOL Plugin 2.0.1 decrypts former S/MIME messages automatically,
but doesn't recognize former plain PGP messages (sent by GPG4Win 2.3.3):

-----BEGIN PGP MESSAGE-----
Version: GnuPG v2
...

4q7o

-----END PGP MESSAGE-----

Icon says "insecure E-Mail" and there is no command to get this ASCII-text decrypted inside of Outlook.
Former GpgOL plugin had dedicated buttons to decrypt plain PGP messages.
Is there a backward compatibility issue?

Details

Version
2.0.1

Revisions and Commits

rO GpgOL
rOb8276a4f3ace Take plain body from OOM and not MAPI
rO093da39ab373 Handle ms-tnef classified PGP/Inline mails

Related Objects

Event Timeline

hs created this task.Sep 22 2017, 3:33 PM
HB1000 added a subscriber: HB1000.Oct 11 2017, 9:38 AM

Do you have any idea about this issue?
Exactly same behaviour here.
Windows 7 Enterprise 64-Bit, Outlook 2010 (Version 14.0.7188.5002, 32-Bit), GpgOL 2.0.1
Tell me if you need any diagnostic logs, ...

pzeier added a subscriber: pzeier.Oct 12 2017, 6:57 PM

Confirmed. Same behaviour and environment as described by HB1000 but with Windows 8.1 x64.
Outlook displays a message inside the mail "decrypting message..." (something like that) and then the message window is blanc as if there is no content.

JochenSaalfeld added a subscriber: JochenSaalfeld.Oct 16 2017, 2:35 PM

Can you relate to the issue described in the GPG4win Forums?

cdeibert added a subscriber: cdeibert.Oct 25 2017, 11:58 AM

Confirmed, this is the exact same problem!

JochenSaalfeld claimed this task.Nov 21 2017, 1:00 PM

@cdeibert, can you may check if this error still exists with the freshly released Version 3.0.1 of Gpg4win?

hs added a comment.Nov 21 2017, 5:17 PM

Just installed Version 3.0.1. From a first glimpse, it seems to work more stable in Outlook context.
But decrypting older plain text messages still fails.
Using GPA (copying PGP ASCII text into dashboard) decrypts contents without error.
-----BEGIN PGP MESSAGE-----
Version: GnuPG v2
...
-----END PGP MESSAGE-----

cdeibert added a comment.Nov 22 2017, 7:33 AM

Hi, also installed 3.0.1. For me decrypting older plain text messages now works!

JochenSaalfeld added a comment.Nov 22 2017, 9:15 AM
In T3419#105989, @hs wrote:

Just installed Version 3.0.1. From a first glimpse, it seems to work more stable in Outlook context.
But decrypting older plain text messages still fails.

Can you elaborate what "older" means? Or how or with what program/plugin they were created, so we may can reproduce this issue?

cdeibert added a comment.Nov 22 2017, 10:47 AM

Hi, VERY odd: My collegue has the exact same installation and environment (actually software deployment-based), she still is suffering to decrypt Mail encrypted with GPG4Win 2.3.2.

JochenSaalfeld added a comment.Nov 22 2017, 10:52 AM
In T3419#106033, @cdeibert wrote:

Hi, VERY odd: My collegue has the exact same installation and environment (actually software deployment-based), she still is suffering to decrypt Mail encrypted with GPG4Win 2.3.2.

This kind of makes sense, since Gpg4win in Version 2.3.2 contained GpgOL in Version 1.4.0. With the step up to Version 3 of Gpg4win, GpgOL was also updated to the ersion 2. With the Release of Gpg4win 3.0.1, GpgOL was implemented in Version 2.0.3. So, a lot of changes in the code happened between GpgOL Version 1.4.0 and 2.0 and another load of fixes came with the Release of Version 2.0.3 of GpgOL.

cdeibert added a comment.Nov 22 2017, 11:05 AM

Unfortunately not, since I am able to decrypt them now (also encrypted with GPG4Win 2.3.2) AFTER the upgrade from 3.0 to 3.0.1 (we both went from 2.3.2 to 3.0 to 3.0.1).

JochenSaalfeld added a comment.Nov 22 2017, 11:07 AM

So to get this straigt:

You had this issue with Gpg4win 3.0.0 and you collegue had them as well with Gpg4win 2.3.2.

You both upgraded to Gpg4win 3.0.1, but your problems disappeared and your collegues problems persisted? And your collogue can't decrypt mails now that have been de- and encrypted whilst using Gpg4win 2.3.2?

cdeibert added a comment.Nov 22 2017, 11:16 AM

We both came from Gpg4win 2.3.2, WE BOTH upgraded to 3.0, as a consequence WE BOTH were unable to decrypt mails once encrypted with Gpg4win 2.3.2 (and actually way older Version of Gpg4win): Please also see https://wald.intevation.org/forum/forum.php?thread_id=1781&forum_id=21&group_id=11 for further description of the issue. Now I AM able to decrypt these mails, my collegue is not (even she also is on 3.0.1).

hs added a comment.EditedNov 22 2017, 1:15 PM

I've sent an email from Outlook using version 2.3.3, to myself. What I see in Outlook with version 3.0.1 is:


-----BEGIN PGP MESSAGE-----
Version: GnuPG v2
hQEMA6jFcgdYY5bVAQgAhWTqExXJVk3aPC5rKYFUeb0NSR+TtChjBzxBrFzQ5qDr
trJiT6o7XoFYDKwdJFXMv81Zcetsu/dOq3dPoCpaQDAtna8xshJDogsx7bOV5bvO
9kLzegZqUk4RzAJLCOTkIISh/Qi6o6kXL4+Iwm17FKfVb0MSAjmrOV50SevrKpD+
PxEYr7BJHRwA9HcYMCb1tvao74AFShZV2olEuwuGvF2nuuqTl6MngKI0Qhteds3F
B6MPOckhHvOCLr3u1z7ld+svggaVFhPyTbXuGxTXAHyieeUr0yf+p4UufdTj3XTn
L/ZeK7l0TKJykbWZmFfZFDClyEDvQx1Vq7ggLuIbh9I/Ab/LkshjC+QGFmfpVaH/
D03ZQv+RStnlI3ZVWvWsAxsaWp/hEsP4RHkmVQXhI4YeRBw1e6TeXzvTvMidjnBC
=oLiX
-----END PGP MESSAGE-----

In the GpgOL ribbon the button shows a question mark and an "unsafe" label.

Feel free to copy the PGP text block above into a normal email and send it to yourself.
Of course you would not get a valid content because it is encrypted to me, but should
see at least some kind of window showing some decryption error or so, and not the plain
ASCII text.

BTW: The deinstallation of version 3.0.0 didn't remove the S/MIME behavior completely.
I had to remove the data in Appdata\Roaming, too. This may help to explain the different
behavior in @cdeibert's case?

JochenSaalfeld reassigned this task from JochenSaalfeld to • aheinecke.Nov 22 2017, 4:08 PM
JochenSaalfeld triaged this task as High priority.

Thank you for your detailed report and the description for the reproducable setup! We will investigate in that issue!

• aheinecke added a project: gpg4win.Nov 22 2017, 5:46 PM

I can't reproduce I sent myself serveral messages in which i pasted a PGP Message and they worked. I tried both HTML and Text plain messages.
To be sure I also installed Gpg4win 2.3.0 and sent myself a message with that and that also worked :-/

I'll take a look at the code tomorrow to check where we could go wrong. If I remember correctly we are just looking at the first 1024 bytes of the mail body to search for the -----BEGIN PGP MESSAGE----- tag and if we find that marker we pass the message on to GnuPG for decryption.

hs added a comment.Nov 24 2017, 5:16 PM

It could depend on the formatting in Outlook (changing hyphens etc.), e.g.
-----BEGIN PGP MESSAGE----- looks sometimes different in Messages.

One message - sent to myself - I see as ASCII text in received folder, but
decrypted in sent folder. That is the source view of the ASCII email, you see, that
the BEGIN token is almost at the end:

<html xmlns:v="urn:schemas-microsoft-com:vml" xmlns:o="urn:schemas-microsoft-com:office:office" xmlns:w="urn:schemas-microsoft-com:office:word" xmlns:m="http://schemas.microsoft.com/office/2004/12/omml" xmlns="http://www.w3.org/TR/REC-html40"><head><META HTTP-EQUIV="Content-Type" CONTENT="text/html; charset=us-ascii"><meta name=ProgId content=Word.Document><meta name=Generator content="Microsoft Word 14"><meta name=Originator content="Microsoft Word 14"><link rel=File-List href="cid:filelist.xml@01D36546.4A047AC0"><!--[if gte mso 9]><xml>
<o:OfficeDocumentSettings>
<o:AllowPNG/>
</o:OfficeDocumentSettings>
</xml><![endif]--><!--[if gte mso 9]><xml>
<w:WordDocument>
<w:SpellingState>Clean</w:SpellingState>
<w:TrackMoves/>
<w:TrackFormatting/>
<w:EnvelopeVis/>
<w:ValidateAgainstSchemas/>
<w:SaveIfXMLInvalid>false</w:SaveIfXMLInvalid>
<w:IgnoreMixedContent>false</w:IgnoreMixedContent>
<w:AlwaysShowPlaceholderText>false</w:AlwaysShowPlaceholderText>
<w:DoNotPromoteQF/>
<w:LidThemeOther>EN-GB</w:LidThemeOther>
<w:LidThemeAsian>X-NONE</w:LidThemeAsian>
<w:LidThemeComplexScript>X-NONE</w:LidThemeComplexScript>
<w:Compatibility>
<w:DoNotExpandShiftReturn/>
<w:BreakWrappedTables/>
<w:SplitPgBreakAndParaMark/>
<w:EnableOpenTypeKerning/>
</w:Compatibility>
<w:BrowserLevel>MicrosoftInternetExplorer4</w:BrowserLevel>
<m:mathPr>
<m:mathFont m:val="Cambria Math"/>
<m:brkBin m:val="before"/>
<m:brkBinSub m:val="&#45;-"/>
<m:smallFrac m:val="off"/>
<m:dispDef/>
<m:lMargin m:val="0"/>
<m:rMargin m:val="0"/>
<m:defJc m:val="centerGroup"/>
<m:wrapIndent m:val="1440"/>
<m:intLim m:val="subSup"/>
<m:naryLim m:val="undOvr"/>
</m:mathPr></w:WordDocument>
</xml><![endif]--><!--[if gte mso 9]><xml>
<w:LatentStyles DefLockedState="false" DefUnhideWhenUsed="true" DefSemiHidden="true" DefQFormat="false" DefPriority="99" LatentStyleCount="267">
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<w:LsdException Locked="false" Priority="73" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful Grid Accent 4"/>
<w:LsdException Locked="false" Priority="60" SemiHidden="false" UnhideWhenUsed="false" Name="Light Shading Accent 5"/>
<w:LsdException Locked="false" Priority="61" SemiHidden="false" UnhideWhenUsed="false" Name="Light List Accent 5"/>
<w:LsdException Locked="false" Priority="62" SemiHidden="false" UnhideWhenUsed="false" Name="Light Grid Accent 5"/>
<w:LsdException Locked="false" Priority="63" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Shading 1 Accent 5"/>
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<w:LsdException Locked="false" Priority="65" SemiHidden="false" UnhideWhenUsed="false" Name="Medium List 1 Accent 5"/>
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<w:LsdException Locked="false" Priority="67" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Grid 1 Accent 5"/>
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<w:LsdException Locked="false" Priority="71" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful Shading Accent 5"/>
<w:LsdException Locked="false" Priority="72" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful List Accent 5"/>
<w:LsdException Locked="false" Priority="73" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful Grid Accent 5"/>
<w:LsdException Locked="false" Priority="60" SemiHidden="false" UnhideWhenUsed="false" Name="Light Shading Accent 6"/>
<w:LsdException Locked="false" Priority="61" SemiHidden="false" UnhideWhenUsed="false" Name="Light List Accent 6"/>
<w:LsdException Locked="false" Priority="62" SemiHidden="false" UnhideWhenUsed="false" Name="Light Grid Accent 6"/>
<w:LsdException Locked="false" Priority="63" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Shading 1 Accent 6"/>
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<w:LsdException Locked="false" Priority="65" SemiHidden="false" UnhideWhenUsed="false" Name="Medium List 1 Accent 6"/>
<w:LsdException Locked="false" Priority="66" SemiHidden="false" UnhideWhenUsed="false" Name="Medium List 2 Accent 6"/>
<w:LsdException Locked="false" Priority="67" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Grid 1 Accent 6"/>
<w:LsdException Locked="false" Priority="68" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Grid 2 Accent 6"/>
<w:LsdException Locked="false" Priority="69" SemiHidden="false" UnhideWhenUsed="false" Name="Medium Grid 3 Accent 6"/>
<w:LsdException Locked="false" Priority="70" SemiHidden="false" UnhideWhenUsed="false" Name="Dark List Accent 6"/>
<w:LsdException Locked="false" Priority="71" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful Shading Accent 6"/>
<w:LsdException Locked="false" Priority="72" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful List Accent 6"/>
<w:LsdException Locked="false" Priority="73" SemiHidden="false" UnhideWhenUsed="false" Name="Colorful Grid Accent 6"/>
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<w:LsdException Locked="false" Priority="21" SemiHidden="false" UnhideWhenUsed="false" QFormat="true" Name="Intense Emphasis"/>
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<w:LsdException Locked="false" Priority="37" Name="Bibliography"/>
<w:LsdException Locked="false" Priority="39" QFormat="true" Name="TOC Heading"/>
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• aheinecke added a comment.Nov 28 2017, 8:47 AM

We have similar reports in our message board.

https://wald.intevation.org/forum/message.php?msg_id=5442&group_id=11

In general HTML should not be a problem as we query the body as plaintext from Outlook and outlook does the HTML parsing. But maybe we are to strict somewhere in our detection code. I'll comb through it and try to break some mails for me ;-)

• aheinecke added a comment.Nov 28 2017, 9:58 AM

I did some experiments with HTML Mails, Leading Text, Trailing Text etc. Everything worked fine for me.

If you could attach a problematic mail (saved with Save As in outlook or better yet with another client as an .mbox file) it might help me to see the problem. I don't have to be able to decrypt that message.

hs added a comment.Nov 28 2017, 10:44 AM

Two versions of the same message as shown in the comment of 24th Nov.

Test.msg31 KBDownload

FW Test.msg36 KBDownload

• aheinecke added a commit: rO093da39ab373: Handle ms-tnef classified PGP/Inline mails.Nov 28 2017, 2:11 PM
• aheinecke added a comment.Nov 28 2017, 2:17 PM

So both your mails did show the exact same behavior for me. The PGP MESSAGE was shown in the mail and not attempted to decrypt.

For these two mails the reason was that Outlook reported their content type as "ms-tnef". This is a proprietary Microsoft Format that I expected for attachments and not for mail.
We handle this now and also look for the PGP Message marker in the body of mails that are reportedly ms-tnef mails. Then decryption was attempted for both your mails :-)

To confirm that this is also your issue and not some artifact of the export / import it would be great if you could replace your \bin or \bin_64 gpgol.dll in the gpg4win installation folder with a version >= gpgol-2.0.4-beta13 from https://files.gpg4win.org/Beta/gpgol/ and try again to confirm if the fix works for you, too.

Thanks!

• aheinecke changed the task status from Open to Testing.Nov 28 2017, 2:18 PM
hs added a comment.Nov 28 2017, 4:00 PM

@aheinecke From a first glimpse, I think we got it. Great work!
I replaced both versions of gpgol.dll as adviced (surprisingly /bin was locked, I expected /bin_64 ).
Thereafter Outlook decrypted all "old" message instantly and without any problems.
Thanks for the effort you spent and the fast reaction time!

cdeibert added a comment.Nov 29 2017, 11:48 AM

Hi, sorry for coming back so late due to lack of time - but good news is: With GPGol 2.0.4-beta15 decryption now also works for us, great! Now we only have to check for a Outlook 2016 stability issue...

Thanks,
Carsten

• aheinecke closed this task as Resolved.Nov 29 2017, 11:51 AM

Thanks for the confirmation.

Now we only have to check for a Outlook 2016 stability issue...

Please let me know if you encounter additional problems with -beta15 that version contains a fix for a possibly random crash and a huge slowdown of Outlook when many mails were selected. I'm currently unaware of additional stability problems.

cdeibert added a comment.Nov 29 2017, 11:56 AM

Fantastic! I have these following issues:

  • Random crash and a huge slowdown of Outlook when many mails were selected ;)
  • Outlook telling me it is out of System Ressources (T3523)
  • Usually once a day Outlook (and all open mails) starts flickering (the app with its windows, not mail bodys) until I restart Outlook
cdeibert added a comment.Dec 12 2017, 7:14 AM

Hi, first of all I want to report back that with beta15 that the following issues did NOT arise anymore, fantastic!

  • Random crash and a huge slowdown of Outlook when many mails were selected
  • Outlook telling me it is out of System Ressources (T3523)

Still from time to time - but less often - I have the mentioned flickering, which also might be a ressource issue, I'll have a eye on it. Unfortunately we did discover a very interesting but frightening issue:

  • You write a message with Outlook 2016 on Exchange Server and GpgOL 2.0.4-beta15, the body contains eg. "I don't like you!!". You close composing this mail, it'll be in the "Draft"-Folder
  • You continue writing your mail from "Draft" and change the body to "I like you!"
  • You encrypt(/sign&encrypt) your mail with the the body to "I like you!"
  • You send this mail, in your "Sent Items"-Folder you'll find your encrypted(/signed&encrypted) mail with the body to "I like you!"
  • The recipient on Outlook 2016/Exchange Server with GPG4Win 2.3.2 & GPGol 1.4.0 will receive your encrypted(/signed&encrypted) mail, but the mail body will contain "I don't like you!!"

Best,
Carsten

• aheinecke mentioned this in T3614: GpgOL: Wrong plaintext body part when saved / sent from drafts.Dec 12 2017, 7:28 AM

I can reproduce that problem and have opened T3614 for this.

• aheinecke added a commit: rOb8276a4f3ace: Take plain body from OOM and not MAPI.Dec 12 2017, 8:38 AM
• aheinecke mentioned this in T3802: GpgOL fails to decrypt email sent from Evolution/Apple Mail via Office365.Feb 21 2018, 4:14 PM
• aheinecke mentioned this in T4267: X.509 mails will not be decrypted.Nov 28 2018, 8:47 AM