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Re: SMTPSecureSocket and Gmail

To: REALbasic NUG <realbasic-nug at lists dot realsoftware dot com>
Subject: Re: SMTPSecureSocket and Gmail
From: Will Leshner <will at haranbanjo dot com>
Date: Wed, 30 Nov 2005 10:18:42 -0800
Delivered-to: realbasic-nug at lists dot realsoftware dot com
References: <54E3A7C8-309A-4B26-8E70-85F85EB31BAF at haranbanjo dot com>

On Nov 29, 2005, at 11:00 PM, Will Leshner wrote:

I think this has come up before, but I'm trying to connect to Gmail with an SMTSecureSocket and I'm not getting very far. The mail never gets sent. But I'm also not getting any errors back. Has anybody successfully connected to Gmail with an SMTPSecureSocket?


To answer my own email, I've looked into this a bit and it would seem that Gmail's recommendation to use port 587 is part of the problem. Apparently the "standard" port for doing SSL over SMTP is 465. I am able to send email if I use port 465. But not reliably. Many times the connection just doesn't finish. But if I use a vanilla SSLSocket, I can connect to smtp.gmail.com every time on port 465. So I've started writing my own SecureSMTPSocket. So far, things look good. I have a very simple SMTP client that appears to be able to send email every time. Which suggests that the problem with SMTSecureSocket is not a problem with SSLSocket itself, but with the SMTP client built on top of it.

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