28 Oct 10 19 - Outlook/Outlook Express attachment mystery

meihobo used Ask the Experts™
Scenario and description of problem.

3 XP_SP3 Systems on standard home network. Let's call them systems X, A, and B.
System X - running Outlook 2003, both A and B running Outlook Express 6
Mail server is - RoadRunner  pop-server.cfl.rr.com  (POP/SMTP)

All mail systems operate normally except X==>A where A does not provide ANY attachments from X.
Meanwhile X==>B,  A==>X, B==>X, A==>B, and B==A all work fine as does X==> outside world mail recipients.

That is to say, system A receives message body contents normally from X, but does not include attachments of any kind.

This is ONLY for emails to A from X.  I can send a message from X to B, then forward it from B to A, and A receives it normally including attachments.

A is somehow discriminating against attached content from X, but only from X.  I have not been able to find any settings on A that would cause this behavior.  

Any suggestions would be appreciated.
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Do you have any antivirus or firewall software enabled on your PC that could be causing interference with the attachments? Maybe try disabling them if applicable and testing.


Disabling AV and firewall has no effect.  Problem is unique to email messages from X to A only.
A can receive identical message and attachment from B with no problem.

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Not without prohibitive expense.  System B can recieve email from X with no problems.  It is OE 6.

Sounds like you may have a message rule on system A that is barring attachments from the sender that is using system X. Do you have any message rules on system A? Also; check what is in your "blocked senders " list.
Did you try receiving the email from X while your AV was disabled. AV programs have the ability of scanning emails and stripping off attachments if it suspects the sender is a spammer or it's on the recipients "black-list". It may be worth checking what the AV program on PC A is capable of, and often when an AV says it is disabled it still may be scanning emails without you knowing it.


I will recheck the suggested conditions and comment on results.  Is it possible that my mail ISP (cfl.rr.com Roadrunner) is filtering from X to only A?

I'd be surprised if your ISP is involved. The filtering has got to be based on the email address, and you've said that Z to B and B to A works.


For Smiffy13
Thanks for your suggestions, here are the results:
 -No message rules on system A
 -No entries on "blocked senders" list.
 -Turning off AV on A no help, same result.

1. Created second email ACCOUNT named "XRM" on A, using same ISP pop-server.cfl.rr.com
    The new XRM account on A recieves attachments without problem from X!

2. Created duplicate of problematic A email account on B.
    The duplicated account on B  blocks attachments from X!!

I believe this would indicate that some mechanism is "protecting" email account on A from attachments from the specific email account on X.  It seems this casts the spotlight on the ISP cfl.rr.com.  Do you agree?


Additional test results - surprising to me.

3. Created second email ACCOUNT named "XRM" on X, using same ISP pop-server.cfl.rr.com
   Original email account on A does not receive attachments from XRM on X.  As would be expected,
   B receives attachments from XRM on X without problem.

To restate - symptoms of originally stated problem exist uniquely from X==>A even from second email account (XRM) on system X.  The ISM theory would require that the ISM identifies something unique to X system other than email account name.  Any ideas would be appreciated.
Does your ISM have a web-mail facility? If so, you could check if the attachment is arriving at the ISM.


Good suggestion.  I will check it out and respond tomorrow.


Results from web-mail tests.
I sent an email with a jpg file attachment from X ==> A with Cc to B

Went to webmail.cfl.rr.com

Opened A email sub-account.
Inbox contained message from A with the following attachment:    winmail.dat in place of jpg file.
I displayed the header and have provided an excerpt immediately below:

****beginning of excerpt****
 msg.txt Content-Type: multipart/mixed; boundary="----=_NextPart_000_0010_01CB7B46.AEADE430"  
winmail.dat Content-Type: application/ms-tnef; name=winmail.dat Content-Disposition:  attachment  
****end of excerpt****

I then Opened B email sub-account on webmail.
Inbox contained the message from A with normal and viewable jpg attachment. !!

Regarding the Winmail.dat attachment:
I saved it to my desktop and researched ms-tnef.

Googled a TNEF Attachment Extractor: Fentun.exe file at Fentun.com that runs on XP.
Loaded the saved Winmail.dat into Fentun.exe (v0.9.5) and was presented with
a window listing the original A attached .JPG file with an Extract option.
Extracted and viewed.  It was the original JPG file intact and viewable.  

To summarize:

X ==> A with cc B
View using webmail.cfl.rr.com
Sub-account B has attachment intact.
Sub-account A has attachment transformed into TNET format and named as Winmail.dat
Winmail.dat contains original jpg file but transformed to tnet.
System A outlook express system did not show any attachment for this test.

in webmail, forwarded B ==> A
as expected, A shows proper attachment on both webmail and Outlook Express.

Finally, I ran another test as follows.
Keeping everything as originally configured before any testing.
I created a new email account on cfl.rr.com on system A.
It is identical to original account except for account name.
Added this new account to Outlook Express on A.
There is no attachment problem for X ==> A on new account.
Althought this is a variation of an earlier test, with similar results,
I still find it a mystery (true to the question title!!).

Somehow something in X or the ISP is identifying something unique
about the original A mail account and converting attachments
form X (and only X) into TNET formatted Winmail.dat files.
There are no user-configurable ISM sub-account settings.

Your suggestion to examine the webmail account contents was excellent.
It uncovered important new clues.  Unfortunately, I am once again stumped!  Any further
ideas would be very much appreciated.  



"Opened A email sub-account.
Inbox contained message from A with the following attachment:    winmail.dat"
Inbox contained message from X with the following attachment:    winmail.dat"


"I then Opened B email sub-account on webmail.
Inbox contained the message from A with normal and viewable jpg attachment. !!"

Inbox contained the message from X with normal and viewable jpg attachment. !!


Perhaps the email address for A on PC X has "send email in plain text" box ticked?

Can you send an email from X's email account to A's email account with an attachment using webmail.


Thanks for the additional comments.
I shall perform these tests/verifications upon my return from a trip, in 3 days.


For smiffy13,

I had issued a cancellation of the A system email account on Nov 3.  My intention was to create a new account with the same name in an attempt to clear out any possible isp blocking.  The ISP requires a 72 hour wait period to delete the account.  It is still indicted as "pending cancellation" status.  I can't create the new account under the original name until it is fully deleted from their database.

In the interim, a companion A email account has been in place and receives all attachments without problem.  The original A system email account name was widely known and used and we would like to restore it when possible.  Hopefully, once deleted, the new account created under the same name will not inherit the blocking characteristics of its predecessor.

I am sorry for the long time gap in comments,  will update ASAP with results of the new account.


Smiffy113's comments, suggestions indicated a good understanding of the complexities of the question.  His comments led to a final disposition of the matter.


For smiffy13:

My ISP never did delete the account in question, even after waiting a full week  I could not, therefore, perform the intended test.  

I have incorporated a work-around to the problem by retaining the second test account and auto-forwarding between them.  This removes the symptom.

I don't think this "mystery" is worth pursuing further since the work-around has eliminated the effect of the problem.  I believe your suggestions led me to developing the alternate "solution" and that you are fully entitled to the associated points.  Thank You for your assistance.

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