I have Google Apps installed and I have tried to set up Outlook 2007 to send messages via SMTP.
I followed the guide, selecting what I believe are all the correct settings. Yes, I am using POP for incoming, that is intentional but I don't believe it should affect outgoing messages.
When I log into gmail (google apps) for my company, I can send a message that has an 8MB attachment (pdf file, not zipped or anything) and it sends fine. However, when I send the same message in Outlook with that same 8mb attachment it fails.
Why am I unable to send an attachment with Outlook via SMTP that I am able to send via Gmail / Google Apps?
The message headers are (some info omitted for privacy):
Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient
domain. We recommend contacting the other email provider for further
information about the cause of this error. The error that the other server
returned was: 552 552 #5.3.4 message size exceeds limit (state 17).
----- Original message -----
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=company.com; s=google;
h=from:to:cc:references:in-reply-to:subject:date:message-id
:mime-version:content-type:x-mailer:thread-index:content-language;
bh=7d4i/Cbt0v0sY3zt5lN6y5CdvxjbRmTBG4AuBuMxtF4=;
b=IJwwxuIEdg1E4zXuGjeDod+1w3RYBBCNzSsqpuX77ih36HSiq++s3ZCQXPeU9CIZVg
K8JPJQu9xjivYYjrRaYwyeowLIu0GIdR2h4kKEkFM/GNC2RFF3VwVgj+gvi5eqVZIuWn
osT5/VEm10IED6B54NPOtGMgFTci6a57zzVKE=
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=google.com; s=20120113;
h=from:to:cc:references:in-reply-to:subject:date:message-id
:mime-version:content-type:x-mailer:thread-index:content-language
:x-gm-message-state;
bh=7d4i/Cbt0v0sY3zt5lN6y5CdvxjbRmTBG4AuBuMxtF4=;
b=LjTecjok5K71Bymp6tZqAL2XCz03hWROV1mTK8Vf2AeEJwtel9ACu9kE5jW5iJqckb
upYKPzoqYLBwAPOzMb9asWoTAZPzC7LMG65eDUc2/ZEvGqXrZs3ziUxwhF4t169yRVuy
/6nm/aAt5uPMLPdobxGTJ8ahOIku1Z3gW+OcvZ6ERk1Av/bvuln09vcnyJIrHGh7eK8n
cbGVxmK0aecgSPgIj2NALbHkyuxwj+LEBRV6uiz3THDjxAiNfsO5UFjV59sD+lVSBT3z
ThOGE8WEXRnKHuP3FuKXyeUxKBZ2CxpWJpvDuS9EsFkln7zkISYEsRA0nUA6GSGi2Z/n
8YUg==
Received: by 10.60.169.197 with SMTP id ag5mr12254920oec.137.1351036287413;
Tue, 23 Oct 2012 16:51:27 -0700 (PDT)
References:
Date: Tue, 23 Oct 2012 19:51:16 -0400
Message-ID: <003a01cdb179$4bb2ca60$e3185f20$@com>
MIME-Version: 1.0
Content-Type: multipart/related;
boundary="----=_NextPart_000_003B_01CDB157.C4A12A60"
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index:
Ac2xVCHGxoC7DDOkQBK3JSXowHb0EQAEB7agAAA/YKAAAIGcQAAAngfQAABAAPAAAFe7gAAAadvw
AALgvLA=
Content-Language: en-us
X-Gm-Message-State:
ALoCoQniMq7Fnh+NlfoWjTJPvKWbkhEaftSaFo9ZVvtRpWufTmhlRDx1a9Jf+wmYcbRh896gygNr
The company I am sending email to is a company that uses Google Apps for Teams. This is their apps admin login. Should I be worried about that message?
My Settings
On the Google apps side I have set my SPF record and set / verified my DKIM key. Here are my outlook settings:
Why am I unable to send an attachment with Outlook via SMTP that I am able to send via Gmail / Google Apps?
