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We host a service which can send emails on behalf of client businesses to end users. These emails must appear to be from the client business, even though they are generated from within our system.

We had previously been using multiple addresses in the From: header whilst also supplying the Sender: header, as described here https://serverfault.com/a/554615.

On around the 3rd of March we started receiving the following bounces consistently from gmail.

smtp;550 5.7.1 [XX.XX.XX.XX 13] Messages with multiple addresses in From: header are not accepted. XXXXXXXXXXXXX - gsmtp

Here is a snippet of the headers we used to send:

Subject: Example Email
Sender: [email protected]
From: <[email protected]>, [email protected]
Reply-To: <[email protected]>
To: <[email protected]>

Does anyone have any idea why gmail would have started blocking the emails and does anyone have a suggestion for a better way for us to send on behalf of another address?

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  • 1
    Holy carp. Well, let's just add this to the unfortunately growing list of things Gmail does wrong.
    – Michael Hampton
    Mar 30, 2017 at 7:03
  • i had the same problem since this morning. since i put only one mail on from tag it works
    – Dioux
    Mar 30, 2017 at 10:45

1 Answer 1

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Hey encode your mail like setEncoding("UTF-8").... it will fixe it

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