Reply-to addresses with very long local-part (username) component
Problem reported by Douglas Foster - 4/12/2026 at 11:53 AM
Submitted
The IETF specs say that usernames should be no more than 64 characters, and a domain name should be no more than 255 characters.    So when I created database tables for logging email addresses, I used a column size of 320 characters.   Recently, I have discovered that this size is not capturing complete data, because some ads have very long reply-to addresses.   The longest in my archive is 317 characters.   I wonder what SmarterMail would do if someone tried to reply to one of those messages.

I am feeling increasingly hostile toward unsolicited advertising, so I think I will create a filtering rule to discard messages that violate the standard so severely.   Don't know what boundary I will use, probably more than 64 characters, but much less than 317. 
J. LaDow Replied
We search for for the list-unsubscribe header and apply a junk mail score to those by default.  If a user wants that mail, they have to go and trust the sender -- it at least helps keep inbox garbage down...

Plus an auto-clean of 30-90 days depending on what the user prefers for Junk Mail folder...
MailEnable survivor / convert --
Douglas Foster Replied
I have researched these long names a little further.   They are all legitimate companies, and one sequence is about a support case with a vendor.   Although the host names are mostly specific to the company in the email addresses, the IP addresses are all owned by Salesforce.com.

I plan to file abuse reports with these companies, on the argument that an excessively long string because a buffer-overflow attack on all receiving systems, to see if they can get SalesForce to change.   A 64-character username permits more than 10^100 unique values, so it should be sufficient.  A 300 character identifier is ridiculous.

SalesForce.com also uses overly long Return-Path names, but the length is less than half of these examples.

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