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.pdf attachments being replaced with winmail.dat in Outlook 2003, Exchange Server 2003

Posted on 2010-11-17
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Last Modified: 2012-06-27
I've seen this posted quite a bit in this site but I'm not finding the answers that I need specific to my problem. sorry!!

Anyway, it appears that when sending to just one domain, our .pdf attachments are stripped and replaced with winmail.dat file that is, as you know, unreadable.  On one user we have attempted to send the e-mail as .html, and plaint .txt, and still it doesn't work.  She used WordPerfect 12 to convert the document to .pdf, it didn't work.  She scanned the document in through a scanner to her Outlook e-mail, renamed and saved the .pdf, sent it and it didn't work and she has scanned it from the printer, to her e-mail and sent it directly from there, and it didn't work.

We found that when we just go to our Sent e-mail and forward it to the intended recipient, it goes through and the attached .pdf is there.

Since this is a large client of ours, I am hesitant to point my finger at them.  I need to be able to tell them exactly what the problem is or, preferably, find a way on our end to keep their system from stripping our attachment the first time around.

Hope this makes sense!  Thank you!!
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Question by:lkretzBK
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Expert Comment

by:darrylka
ID: 34155811
Usually this happens when the recipient isn't using Outlook as their email client.
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Author Comment

by:lkretzBK
ID: 34155944
That's definitely a problem.  Is there a way to work around this problem?
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by:darrylka
ID: 34156323
Do you know what email client they are using?
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by:darrylka
ID: 34156341
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by:bz43
ID: 34156622
Are you sending email in Rich Text Format (RFT)?  If yes, then outlook converts this to WINMAIL.DAT files.  It also puts attachments in this WINMAIL.DAT file.  

Check out this article (only if you are sending as RTF): http://www.quarella.co.uk/email/attachments.html
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Author Comment

by:lkretzBK
ID: 34156679
I don't know what mail software they're using but will do my best to find out.  No...we are not sedning in RTF.  We initially were using HTML and then tried just TXT and neither allowed the attachment to stay put.
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by:bz43
ID: 34157976
This is a link to a Microsoft Knowledge Based article on Outlook and attachments called "How e-mail message formats affect Internet e-mail messages in Outlook".  Maybe it will help:
http://support.microsoft.com/kb/290809/
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Author Comment

by:lkretzBK
ID: 34167735
Thanks but that doesn't help because we are sending in plain text and it's still being stripped and it appears to only be happening from one pc so it must be a setting somewhere.  I've run a "repair" to see if that solves the problem.  Will post back but am still looking for any other info.  

Thanks!!
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Author Comment

by:lkretzBK
ID: 34188347
The repair did not work.  An update did not work.  Messages sent in plain text are still having their .pdf attachment stripped and replaced with a winmail.dat file.  Again, this is only on on pc so I suppose it's user specific.  Should I export her personal folders (pst) and uninstall and reinstall Outlook 2003?  Should I create a new profile - if so, how?

Thanks!!!
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Author Comment

by:lkretzBK
ID: 34519641
Nudge nudge.... since our network is completely bogged down right now, I'm assuming a profile may be to blame, but how do I fix the problem?  Thanks!!
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Author Comment

by:lkretzBK
ID: 34714485
Also, this has now happened to another of our users.  It seems that they only have to resend the original message and the attachment is then received by the intended recipient.  I have yet to find the answer to this problem.
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Author Comment

by:lkretzBK
ID: 35233000
Here's the latest update....I have reformatted a different computer, installed all software from scratch, gave the user a brand new username and therefore a whole new profile, exported her e-mail Inbox ONLY into a .pst file and then imported that into her new Outlook.  AGAIN the problem happened.  Note that the company we're sending to, this only happens from THIS user out of over 20 users.  
Is it possible that one e-mail can cause this to Outlook?  Maybe something that was imported from the inbox?  

I really really need help with this.
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by:Sjef Bosman
ID: 35238807
Can you prove beyond a doubt that txt format is used, e.g. did you send the same message as CC to your personal Gmail address?
When the recipient looks at the source of the message, what do they see?
What *is* the mail client the recipient uses?
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Author Comment

by:lkretzBK
ID: 35241301
We had been using .html and every other person in this firm sends the same way - just this one person with a new install having the same problem which does not occur every time and yet the secretary insists she sends it the same way each time.  The problem also is trying to ask a large client or two to be guinnea pigs on the receiving end.  That's something we can't do.  I will look into those two areas you mentioned and get back on this.
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Author Comment

by:lkretzBK
ID: 35336410
Found out that the receiver is using LotusNotes.  
I had also found the attachments came through fine in my hotmail and gmail accounts but I have yet to hear if they made it through ok to the intended recipients...it looks like they're hit and miss.  Sometimes they get them as intended as .pdf and sometimes they're winmail.dat files.
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Author Comment

by:lkretzBK
ID: 35342654
again..sometimes they receive them sometimes they don't.  I understand this could be a LotusNotes problem and wonder if there's something that I can do to make our attachments go through.  We do not want them to be able to convert our documents so send it pdf.  Maybe a different format such as .tif?

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Author Comment

by:lkretzBK
ID: 35345041
I may have the answer....please let me know what everyone thinks...

If the .NK2 file is corrupt, could that be the cause of the problem?  I had said the only thing I brought over from her last system was her Inbox but I had also copied her NK2 file to the new system.  
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by:Sjef Bosman
ID: 35347372
All I know is that Outlook is know to produce winmail.dat files if it isn't configured for the outside world. The winmail.dat file is in a proprietary format, only understood by MS-software (and some clever tools). How exactly Outlook should be set I can't tell.
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Author Comment

by:lkretzBK
ID: 35347485
I found this in TechRepublic:
What we did to fix winmail.dat issue...
We had the same problem - several Lotus Notes recipients were receiving the winmail.dat file instead of the sent attachments. We tried setting the Outlook mail format to plain text which didn't help at all. Finally figured out that even though we were setting messages to plain text, they were being sent in MIME. Apparently Lotus Notes needs them to be sent in plain text/UUEncode. You can change the recipient send options by right clicking on the email address in the message you're about to send and choosing Send Options. Put a check in the box that says "I want to specify the format for messages to this recipient". Make sure MIME is unchecked and that Plain Text/UUEncode is checked at the bottom. Uncheck the BINHEX box (that's for Macintosh files). You can set this as the default send format for the recipient by going into their contact file, right-clicking on the email address and following these same steps. After making these changes we were able to send any attachment to Lotus Notes recipients. Hope this helps!

I'll give this a try tomorrow and post the results.
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by:Sjef Bosman
ID: 35347542
Ok. I assume that the Notes clients involved are not of the R8.x generation, although they still don't support winmail.dat files, they do handle HTML/MIME mails correctly.

Hope it works!
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Author Comment

by:lkretzBK
ID: 35351153
Those last responses though do not answer why it's only happening to one user out of 12.  Why only e-mails from this one person are having their pdf's converted to winmail.dat.  I'm hoping that removing the nk2 file will solve the problem since when the person replies to a message, she can attach a pdf without it being converted.  Will keep you posted
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Author Comment

by:lkretzBK
ID: 35376713
Upgraded this user to Office 2010 - and again it happened!!!  Again, this is only happening to one user in this whole place.  I am at wits end!!  
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Author Comment

by:lkretzBK
ID: 35377317
I think...this last time...I may have the answer....

Please give me your thoughts....

The emails that are being converted or removed and replaced with winmail.dat are pdf files that have been truncated.  i.e., DOC026~1.pdf

So the answer is that the document was named wayyyy too long which causes it to be truncated on the outgoing mail server; thereby, being flagged.????  
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Author Comment

by:lkretzBK
ID: 35401272
I was wrong.

We shortened the name and still the same problem.  We have MailMarshal as our email filtering program and I have been in contact with them.  They looked at the problem and say it's not anything wrong with their system.

So we're back to the user.  Here are the steps I took:

User had a problem so I researched and found messages needed to be sent in plain text. Tried that.  Didn't work.

Uninstalled and reinstalled her Outlook 2003 software.  Still the same problem.

Reformatted a different computer from a staff member who was let go due to the damn economy.  Reinstalled the operating system, all software, connected the computer to our Exchange 2003 Server and gave the user a new profile with which to log on so that in the event her original profile was corrupt, I wouldn't bring anything with it.

However, I did copy over her NK2 file so she would not have to re-key all the addresses which were not in her address book.

The problem still continued so again we tried the plain text trick and that did not work.

Someone mentioned the NK2 file may be the problem and is why the user could REPLY to a message and attach the exact same pdf file and have it go through.  So I renamed her NK2 file old and she had to start re-keying the addresses.

Again, the original message would be replaced with the winmail.dat file so that wasn't the issue.

So I upgraded her Outlook 2003 to Outlook 2010 and again the problem occurred.

Then I looked on our email history at the server level and found that she was the only employee who was having this problem and her messages were being truncated so that a document that was named:
"PSC 04 15 11 letter to carrier re client wanting to stay home from school.pdf"
would be convered to DOC04~1.pdf  and were located in a winmail.dat file.

So I contacted MailMarshal who webexed into our mail server and looked at the problem.  They ascertained it wasn't the fault of their software converting the file and again was on the user side.  This time the tech webexed into the machine with the problem.  He checked the line that says "When sending messages in Rich Text format to Internet recipients Convert to Plain Text".

Should we also use the Enclose attaching in UUENCODE format when sending in plaint text format??

This is where we're at right now.  Sure would like some feedback.  

Thanks!!
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Author Comment

by:lkretzBK
ID: 35991747
This is so hard to award points as everyone tried so hard.  There was never a solution found.  Nothing worked other than to not allow RTF format on ANY e-mails leaving the server which is not acceptable since it was only one user having the problem.  Is it possible it's a cabling issue?  Just seems like that is the only constant - two different towers, two different profiles, only thing in common is where they're sitting in the office.
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Expert Comment

by:Sjef Bosman
ID: 35994144
Bad vibes in that office?

I sense the pain, but I have no solution other than silly ones like: use any other mail client (e.g. Thunderbird), or migrate to a different mail environment. Dare I suggest Domino or is that too preposterous a suggestion?? Hmm, maybe later...

I hope you find the real solution soon! As for the points: no solution no points...
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Author Comment

by:lkretzBK
ID: 36141851
I've requested that this question be closed as follows:

Accepted answer: 0 points for lkretzBK's comment http:/Q_26621347.html#35347485

for the following reason:

I just simply need to close this but it has never been resolved.
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Expert Comment

by:Sjef Bosman
ID: 36141852
I read about some notes.ini parameters the other day, in this forum, I can't remember who posted it. Can you test if it works for you? If it doesn't, please close the question again...

TNEFEnableConversion=1

See
https://www-304.ibm.com/support/docview.wss?uid=swg21093342
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Author Comment

by:lkretzBK
ID: 36145609
I'm sorry but I can't even try that since we've disabled anyone in the firm from being able to send mail rtf to stop the attachments from being converted.  
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Accepted Solution

by:
lkretzBK earned 0 total points
ID: 36145626
Oh...and I believe the answer is that our Outlook boxes are just taking up too much space on our server and we need to archive and compress the dat file.   Probable corruption due to some mailboxes being over 10 gigs!!!  Thank you everyone for your assistance.
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Author Closing Comment

by:lkretzBK
ID: 36171667
Everyone's assistance is greatly appreciated but there was no definitive answer.
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