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Outlook email with PDF sent to Lotus Notes arrives as winmail.dat, not so simple

Posted on 2008-10-18
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Last Modified: 2013-12-18
I have a user on Outlook trying to send a PDF or Excel attachment to a user on Lotus Notes and it arrives as winmail.dat. That is apparently pretty common but I have been through all the tech notes I can find with no success. I tried to put all steps in the order implemented.

Sender is on Outlook 2003, Windows XP SP2 as are 5 others in the same office. Identical update status, very similar hardware. They have Exchange 2003 SP2 on a SBS 2003 with ISA Server 2004. Also on the server is GFI Mail Security. Everyone goes through this server. The problem is only from this one computer and only as this one users login. That is the puzzle.

He can log in at another computer and it is ok. Another user can log in at his computer and it is ok. They are not on roaming profiles. On the receiving end it does not matter any of 5 recipients all have the same results. I set the contacts in Outlook to plain text only and made sure the email showed that when composed. I set the defaults for all contacts to plain text. I created an entirely new user account for this user and disabled the old user account. I have ESET Nod32 antivirus and have tried with email scanning disabled and with the entire antivirus disabled. The computer is a brand new Dell and was originally on XP SP3. I have had factory installs and SP 3 both create issues before so I formatted the drive and started with a clean XP SP2. I have been testing with common PDFs and Excel files to insure they attachments were not corrupt. I removed and reinstalled Outlook 2003 trying at the new install level and then updated to SP3 and tried. I took it up to Outlook 2007 and tried and then applied all updates to Outlook 2007.

At first I retained the same primary email on the account so that outgoing email would still be under his  email address and have since changed that to  reflect an entirely new email address in case there was filtering on the incoming servers for the recipients.

I am currently waiting on feedback on 16 email tests varying user, computer, text or html, and outgoing email address but I know there is still an issue. I have made so many changes I wanted to verify again exactly what combination worked and not.
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Question by:ksquyres
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SysExpert earned 250 total points
ID: 22750316
Well, your testing methodolgy looks OK, if it is documented so that you know how each email was sent.

Since this only happens to one person, and only on one machine, it is a little weird.

Have you instaled the Office SP3 which updates Outlook client ?

Try that via MS updates ( not windows updates )

I would also check the SP levels of all the relevant outlook clients.



I hope this helps !
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by:Sjef Bosman
Sjef Bosman earned 250 total points
ID: 22757246
When my brother sends me a mail with an attachment, he never fails to make it show up as a winmail.dat.

To stop our discussion, I just installed a utility to read the winmail.dat file:
http://www.eolsoft.com/freeware/winmail_opener/
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Author Comment

by:ksquyres
ID: 22761311
Additional info from new tests. The problem follows the user. The bad user does not have a roaming profile but the problem follows him to the other computer. I did delete the bad users account and gave them a brand new account, new name, everything. They cannot send either html or text format emails with pdfs. They cannot send even if I change their outgoing email to the good users account. The good user can send from either computer, using html or text, going out on their email account or the bad users. It definitely apperar to be user account related but without roaming and with a new user account being created I am puzzled. There are no special considerations at the Exchange server level. Could it be something caused by a server update that affects new user accounts but not ones that were already existing? I will try another newly created account next.  
Thanks Sjef for the comment. The issue is that the recipient is a major customer of the affected user and I am trying to address it on our end if possible. Are you on Notes and your brother Outlook like here?
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by:SysExpert
ID: 22761392
Is the Exchange server mail account also being changed when you create a new user, or are you associating the mail each time , rather than removing and adding in exchange.

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by:Sjef Bosman
ID: 22765164
Indeed, brother is on the Outlook side. I understand your intention, as I tried to convince my brother to modify his settings. Futile... even more pigheaded than I am. :-))

AFAIK, there are settings in Outlook that cause this behaviour. On the other hand, one could say that Notes should be able to accept a winmail.dat file an do something useful with it. Sadly, it doesn't.

Hope this might help:
http://email.about.com/od/outlooktips/qt/et121705.htm
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Author Comment

by:ksquyres
ID: 22768394
When I created the new account I did not associate with any of the old information. Just like a brand new distinct user. I did first use the login on the affected user's computer. I went through another test yesterday. Created another brand new user but logged them in first at another workstation besides the two I have been testing on. All is well as text email and html email. Next will be to try that user acocunt on the affected user's computer. Another item that may have played in this is after the creation of the first two new user accounts that did not work, I had to do updates to the Exchange server in order to get an IPhone to Activesync. That is when the Exchange server went to SP2, and other updates. I don't know why the original existing accounts would have been ok but I had not ruled out that there was an issue on new account creation with Exchange at the level it was at. Now that Exchange is fully updated and the new user account works so far, maybe that will fix it. A few more tests and I will know. Will post results.
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by:Sjef Bosman
ID: 22768493
I really dislike testing on fuzzy systems... You turn your head and there are "updates" installed. Yuck.

I'll keep my fingers crossed!!

Sjef
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by:ksquyres
ID: 22951616
I am posting results from testing. I thought I had the answer but apparently do not. I cleared out all traces of the affected user from all computers he had profiles on. Exchange 2003 isfully updated. I created a brand new user. Logged it in first on a workstation not involved in any previous testing. Outlook 2003 fully updated. All went well. I have this user account under roaming profiles. I logged in at the workstation used in the tests that was not the affected user's primary workstation, again Outlook 03 and all was well. I logged in at the affected user's affected workstation and all was well. Outlook 2007 on this one. Mail was fine as text or html, sending pdf or html attachments. Migrated around to the other workstations randomly and all has been well.

I was going to attribute it to some fluke of the update levels of Server 2003 and Exchange 2003 at the time of the original account creations. Assumed that for some reason the previous existing accounts were created before some offending update was applied.

Now for the fun, it lasted without error for almost 3 weeks but now has returned. Automatic updates is off on both the server and his workstation. He has been using his primary workstation exclusively for this time so it didn't bring anything over from another workstation. No change on the server. The age old question of what changed should be nothing. I will leave this open for a while and post any results. Any thoughts,even random are appreciated.
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by:Sjef Bosman
ID: 22951827
Did you at least give him the winmail.dat converter? It does wonders on my PC: whenever I click to open the attachment, the converter is started atomatically.
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Author Comment

by:ksquyres
ID: 22961420
I have been reluctant to suggest that yet. Two of the recipients would probably be fine with it but it's a corporate structure and several departments and I would have to get probably 10 people to use it. May have to. Thanks

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Author Closing Comment

by:ksquyres
ID: 31507461
Problem still occurs intermittently. Cannot find pattern yet. In need to close question and your both contributing useful material I split the points. Thank you. If I ever find a definitive answer I will post it.
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Expert Comment

by:lkretzBK
ID: 35336564
I am experiencing the exact same problem.  Again, it's Outlook 2003, Exchange Server2003 - all patched sending a .pdf attachment to a recipient using LotusNotes gets converted to winmail.dat.  This also is a large corporate client we're sending to and we cannot keep asking them to do tests with us.  I have been instructed by my higher ups that is a definite no'no.   I have also reformatted and installed all the software from scratch and gave the user a new profile and again the problem happens.

Have you been able to resolve your problem?  lkretz@brownkelly.com if you can respond I'd appreciate it.  Network cabling?  I am at a loss and would really appreciate more insight.
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