Help, numerous problems with gp4win & Outlook 2007

Hi All, I am very new to the world of gnupg encryption and to gpg4win in particular, please bear with me.

I installed gpg4win 2.0 for a couple of users at my job who receive encrypted emails from a client. They are using Outlook 2007 on Windows 7 Pro 64 bit and Outlook is running in online mode. They are able to open encrypted emails with no problems, however they are experiencing some weird behavior in Outlook and Adobe reader since the install.

Adobe reader would generate a cryptic error (that I actually don’t have a record of) when copying and pasting text from a PDF file to an email. Additionally, outbound emails with attachments for (pdf, spreadsheets, text documents), would remain stuck in Outlook’s outbox and would need to be re-opened, re-addressed and edited in the body before re-sending again.

After testing different versions of gpg4win, I found that version 2 (minus Kleopatra during install) resolved these issues. So it seemed…

User “A” was working fine, however she now appears to have an issue with searching for emails in a sub-folder that contains encrypted email. For instance, she goes to the folder at which point she is asked to enter her private key password, she enters the password and proceeds to click into the “search” option on the Outlook toolbar.

She will search for the word “chestnut” and is prompted with approx. 12 results.She now clicks into another folder, her inbox for instance, then goes back to the encrypted email folder and searches for “chestnut” again, only this time no search results are found.

User “B” has the exact same configuration as user “A”, however her issue is different. She can send emails with attachments through Outlook (i.e. PDF, spreadsheets, word documents), but upon doing so a duplicate copy is generated in Outlook’s outbox. The copy remains there and it never sends. This as you’ve probably guessed is confusing the user and making them wonder if the email was sent. Disabling gpg4win add-in in Outlook totally eliminates this problem, but then the user is unable to read encrypted emails.

I have searched the web for answers but haven’t found any substantial solutions, thoughts or suggestions. If you have any, please share them with me, I would greatly appreciate it, thank you!

It just occurred to me upon starting this thread that perhaps gpg4win creates an add-in on all of the applications that I have mentioned in addition to Outlook (Adobe Reader, Microsoft Word, Excel). I’m not sure if that is indeed the case, if someone could confirm that I would greatly appreciate it. In any event, I am going to check that as a possibility on the users’ workstations. I will post and let you know how it goes, thx!