Getting Email Delivered - the ISIPP SuretyMail Blog

Why You Shouldn’t Include Attachments in Email without Asking First

Today I want to talk about a practice that can really get your email in trouble: including attachments in email without first communicating to the recipient that you will be doing so.

There are as many reasons for not sending attachments without first checking as there are different kinds of attachments: .doc files, .xml files, PDF files and, of course, graphics of all kinds.

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One of the primary reasons for not sending attachments via email unless you first advise your correspondent to be on the look out for the attachment is, of course, because the existence of the attachment (by which I mean a file included in the email) is likely to trigger the spam filtering and virus detection programs on the other end, and your email is as likely as not to never make it into the inbox.

Another reason is because even if your email does make it to the inbox, unless the receiver is expecting an attachment from you, they may not open it (in fact, arguably they shouldn’t), for fear that your computer has been compromised and that instead of you sending them a file, it’s a virus that is sending itself out in your name.

Sending out a mass mailing with files attached can cause your mail to run into even more problems, starting way before it ever gets to the other end. Your own ISP may see the large stream of email with attachments emitting from your IP address and assume that you are sending out a virus – intentionally or otherwise – and block your mail from leaving their system.

The best way to ensure that your email gets delivered when it carries an attached file is to first advise the person on the other end that you are about to send a file, and then send it in a separate email. Ask them to confirm that they received it, or send a follow up email letting them know that it was sent, and asking them to confirm receipt.

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« Previously: Why People Who Pay to Receive Your Mailings Still Report Them as Spam

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This article originally written on May 11, 2016, and is as relevant now as when it was first written.