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I try to submit an email, using UploadMessage, with many attachments (total size approx. 19MB) and I jump an error:

"Unable to write data to the transport connection: An error occurred during connection attempt because the connected party did not properly respond after a period of time, or failed to established connection and connected host has failed to respond."

You know that it can be? The mail then you are on gmail.

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  1. Uploading email to an IMAP server is a different thing than sending email. You should use SMTP server if you want to send an email.

  2. I don’t know how your code looks like, you might have simply reached Gmail’s 25MB message limit. Typically Base64 encoding makes the size of the files grow slightly 19 * 1.33 = 25.27

In fact I was able to upload 10MB, 15MB, 18 MB and 19MB messages.

With 19MB Gmail randomly disconnected without any error message. Seems it is Gmail's bug.

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