Attachment sent from Outlook 2010 not shown by recipients

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Not open for further replies.
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
Hi.

We are running Outlook 2010 on a Windows terminal server. We are having some problems sending emails with attachments to some of our customers. This is just regarding some of our customers and i can send the exact same email if i use the Outlook 2003 that i have installed locally on my computer and it gets recievet with attachment and all. The recipients do not recive any attachment at all when using Outlook 2010. Im curious as to why it only happens when i email some customers and not others and why its working with Outlook 2003 and not 2010.

Hoping someone could shine som light on this matter.

Kind regards,

Tommy Svensson
 

larry

Senior Member
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
What message format? The usual cause of "missing attachments" is usually RTF format - and the attachments aren't missing, but encased in a winmail.dat file the other person can't open. (Sometimes the winmail.dat gets removed by the smtp server. )




Is SP1 installed?




First, check the message format - you need to use plain text or html.




Next, clear the autocomplete list or delete the addresses that aren't getting the attachments. To clear the list, go to File, Options, Mail - a button to empty the autocomplete list is near the bottom. If you want to try deleting single names instead, as they come up, select with the arrow keys and press the delete button or use the mouse to click the x on the right side with the mouse.




You can also check the message format setting on the contact - make sure they are not set to always use RTF. Open the contact and double click on the email address.




http://www.slipstick.com/problems/outlook-is-sending-winmail-dat-attachments/ has more about winmail.dat files and where to check the settings (with screenshots.)
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
Part of the problem is the difference between terminal server and a local desktop - that's why it works on your desktop but not for users. It could be mail format as larry suggests - definitely check that first.




The echange admin could configure the server and end the problem forever - but this also affects things that need the TNEF blog, like meeting & task requests and voting.
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
What message format? The usual cause of "missing attachments" is usually RTF format - and the attachments aren't missing, but encased in a winmail.dat file the other person can't open. (Sometimes the winmail.dat gets removed by the smtp server. )

Is SP1 installed?
Yes SP1 is installed.

First, check the message format - you need to use plain text or html.
The oulook client was already set to html.

Next, clear the autocomplete list or delete the addresses that aren't getting the attachments. To clear the list, go to File, Options, Mail - a button to empty the autocomplete list is near the bottom. If you want to try deleting single names instead, as they come up, select with the arrow keys and press the delete button or use the mouse to click the x on the right side with the mouse.
I did the firs one and pressed the clear autocomplete list in outlook file, options, email.

You can also check the message format setting on the contact - make sure they are not set to always use RTF. Open the contact and double click on the email address.
Did this and it was set to RTF, changed it to let outlook decide the best format to send with.

http://www.slipstick.com/problems/outlook-is-sending-winmail-dat-attachments/
has more about winmail.dat files and where to check the settings (with screenshots.)
I have not yet added the registry key as we use some functions that need RTF.

So this is what i have done and it is still not working, something that has changed is that the recipiant now sees the email subject in the color red. But thats the only thing thats changed.

Thank you for your help so far, much apriciated.
 

Forum Admin

Senior Member
If the recepient is seeing the subject in their message list in red, they have an automatic formatting rule to display the messages in red if they met a condition - overdue is the default one. It sounds like either you are flagging items you send or they are using a different autoformatting rule and whatever you did causes your messages to meet the conditions of the rule.

BTW, can they see the attachments now? If so, the cause was the setting you changed and that problem is solved.
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
The problem has somewhat changed.

The PDF attachment is attached through a third party software called Monitor. This software opens up a mail ready to be sent in Outlook, however the recipient cant see the attachment. The email is put i the "sent" folder in Outlook. If i go in there and send it again the recipient can see the attachment, so im suspecting that this third party software is doing some funny buisiness with the mail as it works if i try to send it from the sent folder. What can it possibly do that is making the attachment behave this way?
 

Forum Admin

Senior Member
It's not uncommon for problems like this when 3rd parties create the message.

So the application creates the message - does it comeplete the send or does it just create the message and you need to hit Send? Try saving and closing it then reopening it. You could also try forwarding the draft - if the message is mailformed, outlook will (usually) correct it on the forward.
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
I have now contacted this third party software developer and they say that its not a problem on their end and is refering me to Outlook 2010. Before this summer we used windows server 2003 and Outlook 2007 with the same configuration on the exchange server. For me this points to either something with the operating system or Outlook 2010. I just cant seem to understand what might cause this problem.

Hoping someone could point me in the right direction as im out of things to try.

Kind regards
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
It's not uncommon for problems like this when 3rd parties create the message.

So the application creates the message - does it comeplete the send or does it just create the message and you need to hit Send? Try saving and closing it then reopening it. You could also try forwarding the draft - if the message is mailformed, outlook will (usually) correct it on the forward.
The application does not completly send, it opens up a message with the PDF file attached ready to be sent. What do you mean forwaring the draft?

Kind regards

 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
Hi.

I have done som further tests on this matter.

If i save the mail that is opening, close it and re-open it, it all works just fine and the reciever sees the attached PDF file. If i save just the PDF file, remove it from attachments and add it again it do not work. Does someone have a clue to what is causing this behaviour?

Kind regards,

Tommy Svensson
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
The application does not completly send, it opens up a message with the PDF file attached ready to be sent. What do you mean forwaring the draft?




Kind regards







If you save and close it, then hit forward on the draft (instead of opening it and sending), does it work as expected?
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
Hi.




I have done som further tests on this matter.




If i save the mail that is opening, close it and re-open it, it all works just fine and the receiver sees the attached PDF file. If i save just the PDF file, remove it from attachments and add it again it do not work. Does someone have a clue to what is causing this behavior?




Kind regards,




Tommy Svensson





This indicates the HTML is malformed - saving it and reopening allows outlook to rewrite the message, fixing the errors.




Do you know if the message the recipient receives is large enough to have the attachment hidden on it?
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
This indicates the HTML is malformed - saving it and reopening allows outlook to rewrite the message, fixing the errors.

Do you know if the message the recipient receives is large enough to have the attachment hidden on it?
Ok thank you so much for the info. The mail is only 4 KB and not enough for an attachment so its getting removed earlier.

Any thoughts how to fix it?

Kind regards,

Tommy Svensson
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
No sorry, Without figuring out the cause its hard to come up with a solution. I'm sure it has something to do with the app that is creating the message hough. I just don't know what to do to fix it for good.

I might be foggy because it's late and this is an older thread so the details aren't fresh in my mind... but if saving and reopening the message shows the attachment, how can it be only 4 KB and no attachment?
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
No sorry, Without figuring out the cause its hard to come up with a solution. I'm sure it has something to do with the app that is creating the message hough. I just don't know what to do to fix it for good.

I might be foggy because it's late and this is an older thread so the details aren't fresh in my mind... but if saving and reopening the message shows the attachment, how can it be only 4 KB and no attachment?
Yes im also on to that this app is doing something with the message that gets some of our customers mail servers to discard the attached file. Im not sure if i misunderstood your last note there but if i save and reopen and send the mail, it all gets to the customer and the content can be opened as it should. We tested to use Pipeline tracing on our Exchange server to see if our own server was the problem although we can deliver the attachment to other customers. Sure enough the mail gets through our own Exchange server just fine. I have yet again contacted the developer of this app to see what they have to say about this.

Thanks for all your help.

Kind regards,

Tommy Svensson
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
Hi again.

This issue is still not resolved and i am still in need of help.

The latest update is that this might not be Exchange related.

If i send this mail that this third party software creates it is possible to view the attached PDF-file on one computer but not the other.

Tje recipients says that he cannot view the content on his work laptop using Windows Live Mail but he can view the content on his home computer using Outlook.

I hope that says something to you.

Kind regards,

Tommy
 
Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
Bump!

Regarding my last post about recipient able to view the attached PDF-file on his home computer. He is using Outlook 2003 on his home computer if thats of any help.

Hoping someone could shine some light on this matter.

Kind regards,

Tommy
 

Juliansdad

Member
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
When use Outlook 2010 to send attachments, they end up appearing like Winmap files to AOL recipients and to people what use a MAC to open their email with. The only workaround that I've ever been able to use consistently is to send those people attachments using an online email client rather than Outlook. Sad but true.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
It sounds like the message is being send in RTF format - when you open and save then reopen, outlook is using the defaults for internet mail, which is usually convert RTF to HTML. Live mail can't read rtf but outlook can.

Is the exchange server set to convert rtf to html - its a transport setting. See Outlook is sending Winmail.dat for possible resolution.
 
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