553 5.1.3 Bad recipient address syntax

The recipient address is not a valid email address as far as the server can tell: a missing @, two @ signs, spaces, quotes in the wrong place, a trailing dot, or characters outside what the server permits. The server never looked the mailbox up; it could not parse the address well enough to try.

What the server replies

501 5.1.3 Bad recipient address syntax

Sent by
Any mail server
Type
PermanentRetry fails
About
Recipient problems
Enhanced code
5.1.3

Who sends it

Postfix returns 501 5.1.3 at RCPT TO; Exchange returns 553 5.1.3 "Invalid address" and 501 5.1.3 for addresses with unsupported characters; most servers reject before any lookup.

Why it happens

  • A form that lets users enter "name <user@example.com>" or two addresses in one field.
  • Copy-pasted addresses with a leading or trailing space, or invisible characters.
  • Non-ASCII characters in the local part when the server does not support SMTPUTF8.
  • Angle brackets, commas or semicolons left over from an address book export.

How to fix it

  1. Validate before sending

    Trim whitespace, strip display names, and check the address against a sane pattern (one @, a domain with a dot, no spaces) before it reaches the SMTP layer.

  2. Handle international addresses explicitly

    If you need to send to addresses with non-ASCII local parts, check that the server advertises SMTPUTF8 in its EHLO reply and that your library sends the option.

  3. Look at the raw transaction

    Log the exact RCPT TO line the client sent. The malformed part is usually obvious once you see it.

Check it yourself

These free tools show the records and connections behind this code for your own domain or server.

Related codes

Sources

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