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Outlook 2010 dragging attachments appends extra extension

    Question

  • We have a user who drags attachments from emails they've received into new messages. When they do this the attachment gets an extra extension appended to it e.g. 12345.pdf becomes 12345.pdf.pdf - this happens with any file type. If they then drag and drop the appended file to another email, it get appended again.

    We're using Office 2010 SP1 on W7 SP1

    Is there a solution to this?

    Thursday, October 11, 2012 10:18 AM

Answers

  • Thanks to hvalerio for pointing me in the right direction!

    Uninstalling KB2553488 Office update fixed it for me - Win 7 / Office 2010

    • Marked as answer by fredquango Monday, October 15, 2012 10:49 AM
    Monday, October 15, 2012 10:49 AM
  • I have a solution... uninstalling KB2687315 office update resolve this problem for me (win7 and Office 2007)
    • Marked as answer by fredquango Monday, October 15, 2012 10:50 AM
    Monday, October 15, 2012 10:13 AM

All replies

  • We need to perform the comman troubleshooting steps first:

    1. Launch Outlook with safe mode to check if the issue still persists. If yes, please disable add-ins or macro to test the result again.

    2. Turn off AVG/firewall, especially mail scanner module.

    3. Rename the file to 12345 (no extension and the icon became white). Then drag it to message again to check if it would get an extra extension appended to it again.

    Feel free to post back. Thanks.

    Tony Chen

    TechNet Community Support

    Friday, October 12, 2012 9:35 AM
    Moderator
  • Hi,

    Thanks for the reply!

    To answer your questions, the problem remains when I run Outlook in safe mode and with add ins disabled. Disabling the AV/FW on the machine also makes no difference.

    Just to clarify, if we drag and drop any file from the desktop, My Docs, server share etc. if works fine. It's only when a attachment is dragged from one message to a new one.

    Friday, October 12, 2012 10:58 AM
  • Over the last couple of days we have been getting mail rejections.  We use a Linux mail transport running Mailscanner which objects to double/triple/quadruple  filename extensions.  It is designed to stop mails that have attachments say....  filename.doc.exe which is a common trojan deployment method.  It actually stops any double (or more) file extension.  So when we started getting and sending mail with attachments with filename.doc.doc or filename.pdf.pdf.pdf.pdf Yes it really did add four extensions! I had to find out why pretty quick.  we send a lot of mail with invoices / orders/ statements attached and gradually more and more people in the companies were getting rejections.  It took a while and we tried blaming lots of programmes first (antivirus etc) but we eliminated everything. 

    Not to bore you with all the details of the tests I did, I did find out that It occurred when a user, had an attachment on an email they wished to email to someone else i.e. They would either drag & drop or copy and paste the attachment into a new mail.  At this point when pasted, the filename suddenly aquired a second extension.  This is at the point of creation of the new mail, before even being sent. Not a problem if the attachment was saved off and then attached using insert, or if the original mail was forwarded.

    My machine was fine, as were some others.  My machine had been nagging me for a couple of days to reboot after the latest MS updates. So I did reboot.  Suddenly, I am now having the same problem as others.  Even I could work out that the only thing that had changed was the MS updates (ten in my case)  

    I took a clean machine, installed each update one by one starting with the Office ones. Testing after each install, then rebooting and testing again, then moving to the next update.

    Suffice to say that as soon as I installed KB2687315 I could replicate the problem. 

    As soon as I removed KB2687315 the problem disappeared 

    We are seeing a lot of incoming mail being stopped as well as our outgoing so I think this could turn out to be a major problem!!


    Friday, October 12, 2012 11:36 PM
  • I'm having the same problem, it just started a few days ago.

    We always copy and paste attachments from one email to a new message we are composing but ever since a few days ago it's been duplicating the extension like fredquango says.

    For example, if somebody sends me a file photo.jpg and I copy and paste that onto a new email it will change the file name to photo.jpg.jpg, and if I do it again it becomes photo.jpg.jpg.jpg and so on...

    When I try sending a file without any extension it works on the first email, but when I go and copy it from that email and paste it onto a new email nothing happens, it doesn't attach the file.

    We are having this problem on all of our computers, we are running Windows Vista and 7, they all have ESET Endpoint Antivirus installed but even with it disabled and with Outlook in safe mode we are still having this problem.

    Saturday, October 13, 2012 4:59 PM
  • I just started having the same problem - same deal - must have just started a few days ago.  Am running Windows Vista and Outlook 2010.   I'll try a system restore and see if it is some Windows update causing it.

    Edit:  I did a system restore to 10/9 and that seems to have fixed it.

    • Edited by Morganfey Sunday, October 14, 2012 11:45 AM
    Sunday, October 14, 2012 10:42 AM
  • I have a solution... uninstalling KB2687315 office update resolve this problem for me (win7 and Office 2007)
    • Marked as answer by fredquango Monday, October 15, 2012 10:50 AM
    Monday, October 15, 2012 10:13 AM
  • Thanks to hvalerio for pointing me in the right direction!

    Uninstalling KB2553488 Office update fixed it for me - Win 7 / Office 2010

    • Marked as answer by fredquango Monday, October 15, 2012 10:49 AM
    Monday, October 15, 2012 10:49 AM
  • It seems that this update is really stuffed.

    I can remove the update from Windows 7 machines, and the problem of multiple file extension when pasting goes away.

     

    However on Windows XP machines, this Office/Word/Outlook update wil not either remove, or repair.  Once you have downloaded and installed it that is it, it is there for keeps!


    Steve B

    Monday, October 15, 2012 10:54 AM
  • thank you ,I cant beleive users actual drag attachments from one email to another ,But they do and when is Microsoft going to repair this glitch

    victor arrington

    Monday, October 15, 2012 8:33 PM
  • We just noticed this too. It seems to lead back to KB2687315 (Office 2007) / KB2553488 (Office 2010). These are updates considered critical by MS Security Bulletin 9 Oct 2012, so uninstalling them seems not that good an idea. They patch vulnerabilities in Word for which active exploits are in the wild.

    We have discovered a workaround: if you drag the attachment into the attachment box of the new email no extra extension is added. Most likely because this is Outlook, and the email message itself is edited in Word.

    The attachment box is not present at first though, it appears only after dropping the first attachment. We now delete this attachment and drop the attachment again into the attachment box, and see: no extension added.


    Wednesday, October 17, 2012 11:08 AM
  • Hi, this one is discussed in http://social.technet.microsoft.com/Forums/en-US/outlook/thread/95bf8d3c-5ba7-44f2-b797-c10b4134320a as well.

    Our workaround: if you drag the attachment into the attachment box of the new email no extra extension is added.

    The KB's mentioned are a critical patch for Word, with exploits in the wild.

    Wednesday, October 17, 2012 11:14 AM
  • Wish I had seen this thread last week, I was beginning to think I was the only one who had noticed this problem!!   I have another thread open here with a similar topic and threads elsewhere.

    Some things I have found out so far:

    A few mail checking programmes will reject any mail with a double/triple/quadruple extension (yes I have seen 4 extensions on a mail)  In particular, because we use it, Mailscanner. It is rejecting both incoming and outgoing mail with these extra extensions.  Yes, it is possible to add a rule in the config to allow double extensions but why should I put my networks at risk because an ill designed update has changed the game.

    Yes, you can remove the update on Windows 7 (in our case we use Office 2007 Pro across the Group due to legacy software requirements)  and the problem stops immediately.   BUT on some Windows XP machines the update KB2687315 will not remove. A removal deletes the $uninstall folder from Windows folder, but does not actually remove or restore anything and once that $uninstall fodler is gone you are pretty stuffed at trying to rid your machine of the update.  This laptop I am typing this on has exactly that problem.

    It is incredibly difficult to get to talk to anyone at Microsoft who can help (I am still trying through some contacts I have) Every phone call seems to lead to an Asian call centre where they will not / can not help if your product is not on the list in front of them!

    I know from talking to an engineer in the USA who works for a Mail hosting/processing company that he is seeing a major increase in traffic with multiple filename extensions since last Tuesday.  Fortunately for one of my companies, they do not actually stop mail with duplicate extensions, only double extensions such as .doc.exe

    IdeActive's workaround does work. But does Microsoft seriously expect me to retrain all our users and possibly some clients and suppliers who are having the same problems, to get them out of their copy/paste drag/drop habits, and there are quite a few  that years ago would have been described as Data input clerks....if you get my drift.

    Personally I do think Microsoft broke it, Microsoft should fix it

    Steve

    MS Win7 / Win XP & Off 2007 Pro

    Wednesday, October 17, 2012 11:49 AM
  • Thanks, I was beginning to think I was in a parrallel world and it was only happening in my companies. 

    Yes, that workaround works, but retraining all my users and our customers and our suppliers?  Not quite the answer I want ;)

    Wednesday, October 17, 2012 11:52 AM
  • This is getting ridiculous.  I have now come across one of our users on a laptop, who can not only NOT drag & drop or copy and paste but cannot insert either. 

    When he saves an attachment that he has failed to send to a customer to his desktop using a correct filename (look at the properties of the file and it only has one extension) When he then opens a new mail, and inserts from the menu, the saved file it suddenly appears with two extensions again!!

    On this machine the only option still working is to open the file, then using the send to as attachment menu,this inserts the file properly into an email.

    Wednesday, October 17, 2012 3:12 PM
  • Thanks to hvalerio and fredquango.  We have Win 7 / Office 2010 and removing KB2553488 worked for us, too!  Then we went in and hid the update so it doesn't keep downloading.
    • Proposed as answer by Debit CA Wednesday, October 17, 2012 4:56 PM
    Wednesday, October 17, 2012 4:55 PM
  • I've run into another attachment copy/paste issue that I've isolated down to KB2687315. For only certain messages, if the message item is copied from the mailbox view and pasted into a new message or calendar item, it will not paste as an attachment but will instead paste the message data from the mailbox view along with the column headers:

    From Subject Received 
    <Message Sender> <Message Subject> <Message Received> 

    This seems to be only for certain messages, while others will paste correctly as an attachment. Pasting directly into the attach field works properly though (as was noted in a previous response). Unfortunately that field is not always visible.

    Addendum: upon further troubleshooting, I've narrowed this down to happening on messages that have the pound/hash/# symbol in their subjects. So far it doesn't occur on any others.


    • Edited by Benjy_B Wednesday, October 17, 2012 8:28 PM
    Wednesday, October 17, 2012 7:21 PM
  • Is Microsoft aware of this issue?  I can confirm that in my environment (desktops and laptops running Win7 Pro x64, Office 2007, iManage), I can apply the patch and run into the extension duplication issue when pasting attachments (the extensions keep piling up the more you copy the attachment between emails).

    This needs to be fixed ASAP, I don't like skipping security updates when exploits are in the wild. 

     
    Wednesday, October 17, 2012 7:32 PM
  • I was given an email address at Microsoft to whom I sent a comprehensive description of the faults.  So far not even a reply :(

    Thursday, October 18, 2012 8:37 AM
  • As IDEActive pointed out, these particular updates are supposed to be "critical"  So although removing the update in Windows 7 does solve the immediate problem, I would not recommend this as anything other than a temporary fix. 

    Enough people need to start shouting to get Microsoft to really fix this problem they have caused. 

    IMHO

    Thursday, October 18, 2012 11:07 AM
  • Let me add another vote for a better fix for this issue, and soon. There are all sorts of reasons why people need to drag attachments between e-mails. It seems clear that the recent critical security fixes have caused this artifact of duplicated extensions e.g. "myfile.pdf.pdf" Obviously it's a bug, but as other posters have commented, some AV scanning will block messages with multiple extensions as historically these have been used to hide executable code.
    Thursday, October 18, 2012 5:48 PM
  • I was given an email address at Microsoft to whom I sent a comprehensive description of the faults.  So far not even a reply :(

    Still no sign of a reply from Microsoft, or even an acknowledgement that the problem exists.

    :(

    Friday, October 19, 2012 4:43 PM
  • This issue has been reported to Microsoft and will be escalated for a fix.  As we get any updates I'll come back to the forum thread and provide status. 

    Friday, October 19, 2012 6:57 PM
  • Wow.  Sign of the times I guess.  With the exception of the the smaller shops, it seems hard to get a timely response via email.  Best luck seems to be had in support forums.  If I can't find any updated info about this info by Monday, I'll consider placing a call with them.  It's a bug so I shouldn't have to worry about cashing in a support credit/voucher (I forget how that works, I just call if I need help and that's a rare event). 


    • Edited by Tesfaye_SI Friday, October 19, 2012 7:21 PM
    Friday, October 19, 2012 7:20 PM
  • Well, still no response to my email. 

    But the good news is that it seems someone from Microsoft has picked this problem up on another thread that is running.

    http://social.technet.microsoft.com/Forums/en-US/outlook/thread/95bf8d3c-5ba7-44f2-b797-c10b4134320a

    They respond:

    Gabriel Bratton (MSFT)

    "This issue has been reported to Microsoft and will be escalated for a fix.  As we get any updates I'll come back to the forum thread and provide status.  "

    Tuesday, October 23, 2012 11:45 AM
  • Would have been nice for them to at least acknowlege your email.  However, I'm glad to see that they are going to work on this.

    Tuesday, October 23, 2012 12:38 PM
  • It's not a frequent operation for me but I've had to drag attachments from one message to another on a few occasions. 

    Tuesday, October 23, 2012 12:40 PM
  • We had an issue where we could not copy attachments from one email to another email (or drag/drop) if the attachment file name had a pound/hash/number sign (#).  Uninstalling KB2553488 seems to have resolved it for now.

    I sure hope Microsoft gets this fixed ASAP!

    Tuesday, October 23, 2012 8:42 PM
  • Thanks to the moderator for merging the two threads about this problem together.  As i have been posting in both, I will try to find time to go through and delete my duplicate posts (so it is easier to read the whole thread)

    Steve B

    Wednesday, October 24, 2012 10:19 AM
  • Our users have just noticed this problem happening.  We are running Windows 7 x64 sp1 and Outlook 2010, not really keen on removing a security update.  Microsoft pls could you give us a time scale as to when a fix will be released for this? very annoying for the users.
    Thursday, October 25, 2012 9:19 PM
  • We fully agree with dhymers... not ideal to remove a security hotfix. Please Microsoft let us know what is happening.
    Tuesday, October 30, 2012 8:49 AM
  • We also experience this problem with outlook 2007, looking forward for a fix.
    Wednesday, October 31, 2012 8:40 AM
  • KB2782404 (Attachment file extension is duplicated when added to email in Outlook 2007 and Outlook 2010) describes this issue and includes a link to a related hotfix -- http://support.microsoft.com/kb/2782404

    • Proposed as answer by -veechee- Thursday, November 08, 2012 8:17 PM
    Thursday, November 08, 2012 7:54 PM
  • I have just downloaded and installed the Hotfix on my system.  I confirm it fixes the attachment extension being duplicated.

    Is Microsoft going to release a fix for this via Windows Update in the near future?  I hope so.  If not, can you make a .msi version of this Hotfix so that I can distribute it via GPO?  I don't have any way to distribute a .exe automatically.

    • Proposed as answer by John Kilgore Thursday, November 08, 2012 9:51 PM
    • Unproposed as answer by John Kilgore Thursday, November 08, 2012 9:51 PM
    • Proposed as answer by Mark Peter van Sijll Friday, November 09, 2012 10:30 AM
    Thursday, November 08, 2012 8:16 PM
  • Just got off the phone with MS Support, they gave me the following info.  It might help:

    Microsoft released an updated out-of-band KB for this, so it might need to be approved in the WSUS

     

    Outlook 2007 – KB2757116


     

    Outlook 2010 – KB2757117



    • Proposed as answer by John Kilgore Thursday, November 08, 2012 10:02 PM
    Thursday, November 08, 2012 9:55 PM
  • Attachment file extension is duplicated when added to email in Outlook 2007 and Outlook 2010

    support.microsoft.com/kb/2782404

    Thursday, November 08, 2012 10:09 PM
  • I have just downloaded and installed the Hotfix on my system.  I confirm it fixes the attachment extension being duplicated.

    Is Microsoft going to release a fix for this via Windows Update in the near future?  I hope so.  If not, can you make a .msi version of this Hotfix so that I can distribute it via GPO?  I don't have any way to distribute a .exe automatically.

    I can't speak to the plans for release plans for this hotfix with regard to Windows Update, but I can tell you how to extract the MSP file from the hotfix executable and use an msiexec command line to install it.

    1) Download the appropriate hotfix via the links in KB2782404.

    2) Extract the contents of the downloaded hotfix executable to a temporary folder, using a command line similar to the following (references to "C:\KB2687556" and "C:\KB2687556\extracted" are examples which can be changed to match your environment):

    C:\KB2687556\office2010-kb2687556-fullfile-x86-glb.exe /extract:C:\KB2687556\extracted

    3) Use command lines similar to the following to silently install the updates using the Wndows Installer and create a related verbose log file in the temp directory. Change "/QN" to "/QB" for an installation with only a basic progress indicator (references to "C:\KB2687556", "C:\KB2687556\extracted", and log file names are examples which can be changed to match your environment):

    %windir%\System32\msiexec.exe /P C:\KB2687556\extracted\kb2428677-x-none.msp /QN /L*V %temp%\kb2428677_x_none.log

    %windir%\System32\msiexec.exe /P C:\KB2687556\extracted\word-x-none.msp /QN /L*V %temp%\word-x-none.msp.log


    Thursday, November 08, 2012 10:15 PM
  • I can confirm that the hotfix does correct the problem.  My test was done in my XenApp environment: Win 2k8 R2, XA 6, Office 2007 w/SP2.  No reboots were necessary. 

    Friday, November 09, 2012 4:03 PM
  • A KB article has been published with the Word updates that need to be installed to fix the issue, http://support.microsoft.com/kb/2782404  


    Tuesday, November 13, 2012 7:17 PM
  • Unfortunately, the rollup doesn't appear in WU Catalog.  :(  I released the hotfix to all machines using a startup script.
    Tuesday, November 13, 2012 7:47 PM
  • I think you meant to respond to someone else?  In my post, I was responding to Eric to confirm that the Word 2007 hotfix (KB2687537) corrects the issue in Outlook. 

    Tuesday, November 13, 2012 7:55 PM
  • It seems that KB2687556 fixed our Outlook file attachment copy/paste from existing e-mail to new e-mail issue as well. Files with the "#", or hash tag, pound symbol, can now be dragged/dropped or copy/pasted without any issues.

    Can anybody else confirm that, please?

    Thank you everybody for your work!


    • Edited by J L C L Wednesday, November 14, 2012 11:04 PM
    Wednesday, November 14, 2012 10:58 PM
  • Does anyone know if there are plans to release the update that fixes this via WSUS please?
    Thursday, December 20, 2012 3:00 PM