I don't receive some forwarded e-mail (with attachments) Doesn't get delivered to my e-mail

Posted on 2007-09-28
Medium Priority
Last Modified: 2012-08-14
I have an unusual problem with my e-mail. I seem to be getting e-mails OK except when someone tries to send me an e-mail with an attachment. Actually - I get e-mails with attachments as long as the sender composes and then attaches the file (typically a .pdf). If, however the sender forwards the e-mail with the attached file I won't get it. Even worse than that - the sender doesn't get any warning or errors that the message (with attachment) did not get delivered.

I'm using a hosted e-mail provider and they don't seem to be able to solve this problem. I would really like to find out the answer to this one - as I am completely stumped why regular e-mails get delivered, regular e-mails with manually attached files get delivered, but e-mails that have been forwarded (with attachments) are not delivered. Can anybody help me?
Question by:stanpasquale
LVL 63

Assisted Solution

SysExpert earned 800 total points
ID: 19981648
Tell everyone that they need to manually attach the files, or get a different host.

They should be checking their SPAM software/ filters and similar that could be blocking stuff.

It;s their problem, and if they can't get it fixed, find  a better hosting service.

I hope this helps !

Accepted Solution

-Mystique- earned 1200 total points
ID: 19982871

Improve Your Email Delivery Rates

An excerpt from another article about email delivery failures:
When you get mail from a "MAILER-DAEMON" or a "Mail Delivery Subsystem," with a subject similar to "Failed Delivery", this means that a message which you sent was undeliverable and has been "bounced" back to you. These messages are produced automatically and usually include a reason for the delivery failure. Bounced messages normally consist of two parts. The first contains the reason for the bounce; the second contains your original message. The most common reason for a failed delivery is that the email address you entered is not valid. If the Mailer Daemon says that the account does not exist, double check the spelling of the address you entered. A single misplaced letter can be enough to cause a failed delivery. If the message continues to be bounced back to you, you may want to verify that the account has not been closed or moved.

Hotmail Fails To Deliver Up To 81% Of All Attachment Emails
Informative article, illustrations accompanying explanations of what happens, comments, and moire

Perhaps the cause is at the sender's end, this pdf explains such situations.
We show how automated processing of the email logs recorded on the “smarthost” provided
by an ISP for their customer's outgoing email can be used to detect this spam

another possible contributor to the problem
Outlook Attachments Blocked or Restricted
one excerpt
Once the MS Security update is applied - a list of unsafe file types (Level 1 file types) is loaded, and incoming emails with attached files are pre-screened against the list.  The attachment's file name extension (the three characters after the period) is checked against the list's unsafe files types, such as exe, com, etc.  Depending on it's extension, there are three possible outcomes:

another excerpt
The Effects of the MS Security Patch on Emails
Forwarding Emails with L1 or L2 Attachments - all Level 1 and Level 2 attachments are removed from forwarded emails, before the email is sent !!
This article also discusses how to correct the problem if it's due to Outlook's MS security patch.

One of the general rules of email security guidelines given in this article may show why attachments are often regarded as potentially dangerous and delivery prevented.
this rule quoted from the article as follows.
Be in double measure suspicious of attachments that have been forwarded to you - even by someone you know.

One example given in this article:
Your friend emails you a cute attachment with the file name "kitty.exe". In their message, they tell you they've tried it themselves, it's really cute, and it's "OK to open". You check with your friend, and yes indeed, he or she did send it, and they assure you "it doesn't have a virus." The trouble is, it contains a delayed action Trojan-horse along with the cute kitty. When you open it, the kitty does something cute, but the Trojan is also installed on your computer. You and your friend will not find out about the Trojan until later, if ever.

Another excerpt that helps explain situations with attachments that aren't obvious on the surface.
Attackers often disguise malicious attachments by using double extensions, for example, "message.txt.lnk" or "picture.gif.vbe". Unless you've changed your Windows configuration though, *.lnk, *.vbe and several other extensions are always hidden. The file names that you see are just "message.txt" or "picture.gif". Those files - *.txt and *.gif files - seem safe enough. Windows knows they are *.lnk or *.vbe files though, not text or picture files at all. When you "open" them though, Windows blindly does exactly what the attacker had in mind, and the damage is done.

Advice from the above article on sending emails with attachments so that they get delivered
Sending Email with Attachments
Avoid sending attachments if the same information can be sent as a plain text or RTF.
Rather than sending a .doc file as an attachment, it's often best to cut and paste the .doc content into your email as text.
You can also convert .xls files to .csv (comma-delimited format) before sending, thus minimizing the risk of spreadsheet macro and script viruses.
Only if it is essential to retain document formatting, embedded objects, etc., should you or your correspondents send unsafe file types - and then only if you have recently run an updated virus scanning program that includes protection from macro viruses.

excerpt from the above article
9. Spamming as a result of forwarding email.
Forwarding emails can be a great way to quickly bring someone up to speed on a subject without having to write up a summary email, but if you aren't careful, forwarding emails can create a significant security threat for yourself and the earlier recipients of the email. As an email is forwarded, the recipients of the mail (until that point in time) are automatically listed in the body of the email. As the chain keeps moving forward, more and more recipient ids are placed on the list.
Unfortunately, if a spammer or someone just looking to make a quick buck gets a hold of the email, they can then sell the entire list of email ids and then everyone will start to get spammed. It only takes a few seconds to delete all the previous recipient ids before forwarding a piece of mail, and it can avoid the terrible situation of you being the cause of all your friends or coworkers getting spammed

How to forward emails "As Attachments"  
If you ever need to forward an email to ReadNotify staff, we always need it "As an Attachment" (not "inline"). Click on your email program in the list below to find out how to do this. (excerpt pasted from the link above)

Advice for Using Email Attachments

Top 10 Email Tips

another possible contributor to the problem
Reverse DNS mismatches mark Exchange email as spam
Many Internet Service Providers and email providers, such as AOL and Hotmail, attempt to block spam by using reverse DNS lookups on incoming email. Reverse DNS lookups are used to validate that the IP addresses of originating servers match the origin information in the actual email messages.
By and large this is a good idea, but there are a few places where it falls apart.

One possible piece of useful advice excerpted from above link
This is nothing to do with Exchange but everything to do with the new security features in Outlook to prevent spread of viruses using program extensions.
I suggest ZIPing or renaming files up before sending certain attachments, most data and Office files will send ok (except MDB files). Its program files such as EXEs, COMs, PIFs, SCRs, VBSs that can be a threat.

Zipping an attachment is something that would be worth trying too.  Hope something here helps you solve the problem


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