How To Cross The 1000-Character SMTP Barrier With Quoted-printable

Sent a long email with a text attachment that got messed up? Did you know that SMTP has a 1000 character limit – it’s well documented but then again, who reads the manual?

Here’s a nice post from Shifa that explains the problem and how to solve it.

Noob Snippets

While sending some lengthy text files as email attachments, I discovered that some of my sentences were broken mid-word into new lines. Turns out, SMTP protocol allows only 1000 characters per line. Each line is to be wrapped at 998 characters by a CRLF (rn). Now, most email platforms such as Mandrill and SendGrid follow this rule, but Gmail seems to bypass it somehow. This prompted me to further look into workarounds to keep the attachment formatting as is.

Action Mailer Rails Guides tell you that the Mail gem automatically guesses the attachment content type, encoding and creates the attachment. The default content-type is ‘plain/text’. So I tried playing around with different content-types/ mime-types, for example text/tab-separated-values (Since I had a tab separated format) hoping they would be treated differently from plain text. But that didn’t do the trick.

After reading up some more about the SMTP line limits

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