Checkout via telnet what exactly you are connecting to via port 25, it's not a GMail server with that 220 ****************** string in there. I suspect both ports 587 and 465 are being blocked and port 25 is being redirected.
Here's how I have the setup and here's a couple of session logs up to sending the AUTH command.
(b) -SMTP STARTTLS -
Server host name: smtp.gmail.com
Server TCP/IP port: 587
SSL/TLS: via STARTTLS
Enable server certificate fingerprint tracking: checked
SMTP Authentication: Login to the SMTP server using POP3
username/password (the GMAIL-POP3-definition has been chosen)
(c) - SMTP via SSL -
Server host name: smtp.gmail.com
Server TCP/IP port: 465
SSL/TLS: via direct ssl connection
Enable server certificate fingerprint tracking: unchecked
SMTP Authentication: Login to the SMTP server using POP3
username/password (the GMAIL-POP3-definition has been chosen)
--- Mon, 10 Sep 2007 07:27:25 ---
Connect to 'smtp.gmail.com' port 465, timeout 300.
07:27:25.218 [*] Connection established to 64.233.163.111
07:27:26.515 [*] SSL/TLS session established: 3DES, CBC mode, keysize 192 bits
07:27:26.515 [*] Certificate user is cn=smtp.gmail.com, o=Google Inc, l=Mountain View, sp=California, c=US
07:27:26.546 [*] Certificate is valid from Mon Jul 30 16:58:07 2007 to Tue Jul 29 16:58:07 2008
07:27:26.546 [*] Certificate fingerprint is 32666C0ADC4F2DF9832EB4AA22A7E0E7
07:27:26.546 >> 0040 220 mx.google.com ESMTP m1sm4375875nzf\0D\0A
07:27:26.546 << 0020 EHLO [192.168.1.5]\0D\0A
07:27:26.625 >> 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:27:26.625 >> 0019 250-SIZE 28311552\0D\0A
07:27:26.625 >> 0014 250-8BITMIME\0D\0A
07:27:26.625 >> 0022 250-AUTH LOGIN PLAIN\0D\0A
07:27:26.625 >> 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:27:26.640 << 0012 AUTH LOGIN\0D\0A
--- Mon, 10 Sep 2007 07:39:30 ---
Connect to 'smtp.gmail.com' port 587, timeout 300.
07:39:30.171 [*] Connection established to 64.233.163.111
07:39:31.265 >> 0040 220 mx.google.com ESMTP i5sm4387117nzi\0D\0A
07:39:31.265 << 0020 EHLO [192.168.1.5]\0D\0A
07:39:31.343 >> 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:39:31.343 >> 0019 250-SIZE 28311552\0D\0A
07:39:31.343 >> 0014 250-8BITMIME\0D\0A
07:39:31.343 >> 0014 250-STARTTLS\0D\0A
07:39:31.343 >> 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:39:31.359 << 0010 STARTTLS\0D\0A
07:39:31.437 >> 0030 220 2.0.0 Ready to start TLS\0D\0A
07:39:31.640 [*] SSL/TLS session established: 3DES, CBC mode, keysize 192 bits
07:39:31.640 [*] Certificate user is cn=smtp.gmail.com, o=Google Inc, l=Mountain View, sp=California, c=US
07:39:31.640 [*] Certificate is valid from Mon Jul 30 16:58:07 2007 to Tue Jul 29 16:58:07 2008
07:39:31.640 [*] Certificate fingerprint is 32666C0ADC4F2DF9832EB4AA22A7E0E7
07:39:38.046 << 0020 EHLO [192.168.1.5]\0D\0A
07:39:38.156 >> 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:39:38.156 >> 0019 250-SIZE 28311552\0D\0A
07:39:38.156 >> 0014 250-8BITMIME\0D\0A
07:39:38.156 >> 0022 250-AUTH LOGIN PLAIN\0D\0A
07:39:38.156 >> 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:39:38.156 << 0012 AUTH LOGIN\0D\0A
<p>Checkout via telnet what exactly you are connecting to via port 25, it's not a GMail server with that 220 ****************** string in there.&nbsp; I suspect both ports 587 and 465 are being blocked and port 25 is being redirected.</p><p>Here's how I have the setup and here's a couple of session logs up to sending the AUTH command.&nbsp;</p><p>&nbsp;</p><p>(b) -SMTP STARTTLS -
&nbsp; Server host name: smtp.gmail.com
&nbsp; Server TCP/IP port: 587
&nbsp; SSL/TLS: via STARTTLS
&nbsp; Enable server certificate fingerprint tracking: checked
&nbsp; SMTP Authentication: Login to the SMTP server using POP3
&nbsp; username/password (the GMAIL-POP3-definition has been chosen)
(c) - SMTP via SSL -
&nbsp; Server host name: smtp.gmail.com
&nbsp; Server TCP/IP port: 465
&nbsp; SSL/TLS: via direct ssl connection
&nbsp; Enable server certificate fingerprint tracking: unchecked
&nbsp; SMTP Authentication: Login to the SMTP server using POP3
&nbsp; username/password (the GMAIL-POP3-definition has been chosen)
</p><p>
--- Mon, 10 Sep 2007 07:27:25 ---
Connect to 'smtp.gmail.com' port 465, timeout 300.
07:27:25.218 [*] Connection established to 64.233.163.111
07:27:26.515 [*] SSL/TLS session established: 3DES, CBC mode, keysize 192 bits
07:27:26.515 [*] Certificate user is cn=smtp.gmail.com, o=Google Inc, l=Mountain View, sp=California, c=US
07:27:26.546 [*] Certificate is valid from Mon Jul 30 16:58:07 2007 to Tue Jul 29 16:58:07 2008
07:27:26.546 [*] Certificate fingerprint is 32666C0ADC4F2DF9832EB4AA22A7E0E7
07:27:26.546 &gt;&gt; 0040 220 mx.google.com ESMTP m1sm4375875nzf\0D\0A
07:27:26.546 &lt;&lt; 0020 EHLO [192.168.1.5]\0D\0A
07:27:26.625 &gt;&gt; 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:27:26.625 &gt;&gt; 0019 250-SIZE 28311552\0D\0A
07:27:26.625 &gt;&gt; 0014 250-8BITMIME\0D\0A
07:27:26.625 &gt;&gt; 0022 250-AUTH LOGIN PLAIN\0D\0A
07:27:26.625 &gt;&gt; 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:27:26.640 &lt;&lt; 0012 AUTH LOGIN\0D\0A
</p><p>&nbsp;</p><p>--- Mon, 10 Sep 2007 07:39:30 ---
Connect to 'smtp.gmail.com' port 587, timeout 300.
07:39:30.171 [*] Connection established to 64.233.163.111
07:39:31.265 &gt;&gt; 0040 220 mx.google.com ESMTP i5sm4387117nzi\0D\0A
07:39:31.265 &lt;&lt; 0020 EHLO [192.168.1.5]\0D\0A
07:39:31.343 &gt;&gt; 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:39:31.343 &gt;&gt; 0019 250-SIZE 28311552\0D\0A
07:39:31.343 &gt;&gt; 0014 250-8BITMIME\0D\0A
07:39:31.343 &gt;&gt; 0014 250-STARTTLS\0D\0A
07:39:31.343 &gt;&gt; 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:39:31.359 &lt;&lt; 0010 STARTTLS\0D\0A
07:39:31.437 &gt;&gt; 0030 220 2.0.0 Ready to start TLS\0D\0A
07:39:31.640 [*] SSL/TLS session established: 3DES, CBC mode, keysize 192 bits
07:39:31.640 [*] Certificate user is cn=smtp.gmail.com, o=Google Inc, l=Mountain View, sp=California, c=US
07:39:31.640 [*] Certificate is valid from Mon Jul 30 16:58:07 2007 to Tue Jul 29 16:58:07 2008
07:39:31.640 [*] Certificate fingerprint is 32666C0ADC4F2DF9832EB4AA22A7E0E7
07:39:38.046 &lt;&lt; 0020 EHLO [192.168.1.5]\0D\0A
07:39:38.156 &gt;&gt; 0051 250-mx.google.com at your service, [209.128.94.2]\0D\0A
07:39:38.156 &gt;&gt; 0019 250-SIZE 28311552\0D\0A
07:39:38.156 &gt;&gt; 0014 250-8BITMIME\0D\0A
07:39:38.156 &gt;&gt; 0022 250-AUTH LOGIN PLAIN\0D\0A
07:39:38.156 &gt;&gt; 0025 250 ENHANCEDSTATUSCODES\0D\0A
07:39:38.156 &lt;&lt; 0012 AUTH LOGIN\0D\0A
</p>