Why sometimes your email attachments don't get through.

The problem of undelivered email attachments is undeniably annoying. An important document goes missing from the email, or your contact claims they’ve never received it – almost always right before a deadline.

Initially, you may assume a simple mistake, that the attachment was never included in the first place. But when you resend the email and the attachment still isn’t received, it becomes obvious that something more serious is happening.


Aggressive email filtering

In almost every case, the attachment will disappear as your email reaches the recipient. Modern email security systems scan every incoming message to determine if it is spam (unwanted marketing messages) or contains viruses. If either condition is met, your message is “quarantined” (it disappears into a black hole, never to be seen again), or the attachment is deleted while the rest of the message is delivered successfully.

When an attachment goes missing, the problem is almost certainly at the receiving (recipient's) side.

Why does your attachment disappear?

Spam filters are like a magic black box, filtering messages according to rules created and maintained by the manufacturer or the system administrator for each business you email. The trouble is that these rules are kept a secret to stop cybercriminals getting around them. There are a few things you can do to avoid your messages being deleted – this article shows you how.

Most email security systems can be customised too. It is not uncommon for IT systems administrators to block email attachments that contain macros, for instance,  helping to reduce the risk of malware installing itself on the network.

Some security experts take their safeguards a step further, banning certain attachment types altogether. It has been known for Microsoft Office files (Word, Excel, PowerPoint) to be banned completely, whether the document contains a macro or not.

If a particular file type has been banned, your attachment will never be delivered – no matter what you do.

What can you do to get around these email filters?

Because your customer controls their email security settings, you can do nothing to force that attachment to be delivered. So there’s no point in pulling your hair out, having your boss step in, or screaming at your IT guy. 

All you can do is ask your contact to supply a workaround. That may involve sending the attachment in a different file format (PDF instead of MS Word) or use a file-sharing service like Dropbox or Google Drive where the recipient can download the file using a web browser.

Be aware - you may run into problems trying to explain the problem to your recipient as they may be totally unaware of corporate email rules. Never be afraid to tell the receiver about the problem and its cause, but be prepared initial surprise and bafflement on their part. In reality, you are doing them a favour by helping them better understand the limitations in place at their workplace - and to explain why other senders have similar problems. You should send them a link to this blog post.

In the meantime, feel free to suggest workarounds such as using Firefox Send (our favourite) to securely and easily share the file, but ultimately the issue is with your recipient – and you are reliant on them (or their IT team) “fixing” it.

So next time your attachments fail to reach the addressee, speak to them first – otherwise, you may end up on a wild goose chase trying to fix a problem that doesn't exist.

For more help and advice on email related issues – and how your business can better protect itself, please get in touch