Sudden Failure of AmazonSES for some...

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So what is strange is on the same server, with the same PHP version and INI settings as well as the same API Key/Secret combination is failing on sending through AmazonSES. This is a WordPress website set up with PostSMTP to send out authenticated outbound emails. I have tested an older API Key/Secret combination on the same system with the same results of it failing to be able to send outbound messages. Yet another website on the same system is able to send outbound messages.

In the failing system, the transcript ends with: 554 Transaction failed: Missing start boundary.

Same server connection, port 587 using StartTLS. I have made sure that the credentials are correct as well as attempted generating new ones for use within the system. Double checked the policy of the user that is generating the API keys to ensure it isn't being restricted in that manner.

  • For some reason the user that was still active in the system some how stopped working. After recreating for a 3rd time the new credentials finally started working for this. Why they where working one day and stopped the following day I do not have an answer for this. Nothing in the system said that the credentials shouldn't have worked.

    Anyone have any thoughts?

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Based on the error message you're seeing, it seems the issue may be related to the formatting of the email message body rather than the Amazon SES configuration. The "Missing start boundary" error typically occurs when the MIME structure of the message is invalid. A few things you could check:

  • Make sure the message body and any attachments are using the correct MIME type boundaries (e.g. multipart/mixed or multipart/alternative).
  • Verify the message encoding is set properly, usually UTF-8.
  • Check for any special characters or encoding in the message body that could interfere with the MIME structure.
  • Try sending a very simple test message with just text/plain body and no attachments to isolate if it's a formatting problem.

It's strange that other sites on the same server are able to send successfully. Some things to cross-check between the working and non-working sites:

  • PHPMailer or library version in use
  • Message body/attachment formatting
  • IAM permissions for the API keys
  • Network connectivity/routing between server and SES

Let me know if simplifying the message structure or comparing configs between sites provides any clues. Sometimes minor differences in message formatting can trigger errors. Happy to provide code samples if needed.

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  • While that was in the transcript, I originally thought that it had to do with something about that. In my testing I created a 2nd set of credentials to test and those didn't work. So I continued going down a rabbit hole. Kept seeing it also say credentials not correct. I finally fully deleted the existing creds for that system and then created new ones and it started working again. No msg stating that creds started failing or that they had been deactivated.

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