I'm using Outlook 2007 to send/receive email via my Google Apps (GA) account, effectively using gmail as my exchange server. I'm also using the google sync tool to synchronize the information between Outlook and GA. Everything works perfectly, except:

Sometimes, when I send an email to someone via Outlook, it goes in to the recipients spam folder. If I send them the exact same email using the GA gmail interface (from within Chrome, IE, or Firefox), and send it to the exact same address, they get the email just fine.

My assumption is that theres something thats either not configured correctly in Outlook, or that Outlook is adding to the emails that the spam filters are picking up on.

Any thoughts?

Here's the email header from the google account:

m Jeff Bob Wed May 26 18:38:12 2010
X-Apparently-To: bob_jeff@yahoo.com via 66.196.100.83; Wed, 26 May 2010 11:38:12 -0700
Return-Path: <jeff.bob@jeffbob.com>
Received-SPF: neutral (mta1066.mail.ac4.yahoo.com: domain of jeff.bob@jeffbob.com is neutral about designating 74.125.83.47 as permitted sender)
X-YMailISG: m.Q4XYYcZApgHPBTMtAsmKQwP1HIT0OGv1UM0knuFctzk.ExJn d9kjEfq8Zeq3PJJOuyJajMyNPSrUZWxY86yfLbl4koqXuw0nW5 9qoskSg4_plEeqjA1CEGIi7o18xmbwgf925xfxDdBGHoR1ZaVk If3jzwd7QlOSCl8DKU8TOSzHlYyZQ.BRwM7xdyX3JDqlqMvOst Q6B3bGteJ6NYcn3RPPBhINxSNKlorkWW1yulrU5BeF_pRacWvR Ndtb.lXV27I99QITCTdyju10Xz5dIjJdx_JazsCMT2s_yG_7tt qIm9a_VqhlOsFAjjEmUxfNA0W2mWabIZWkPSjQ6ZONqUAGkhbk 63CR8j_chFVCemzPB.0p9J7zG5qcfd5REKuRn0tHn1OeDH.fZz PaJxZlNX481KJuFlWYXvZyiuoXdLwe1181Emm0HXWiSZKv1o37 4qk7HTl_EGFajIeLKe.RZcbcvVRCh8Nwo.deGw4MM_RcVgrRjF v2QOWra_D4QvFKlQcdyERRDdFmjPovuRR29YKjpiRaRhSv8rt7 F7od0eIdFD5mX4eVRxL9tta1A2jTUD1cE5tSAxhXJz0cuYKVgY nqS.Ng4RdhAAJFdSe1lcUSk-
X-Originating-IP: [74.125.83.47]
Authentication-Results: mta1066.mail.ac4.yahoo.com from=jeffbob.com; domainkeys=neutral (no sig); from=jeffbob.com; dkim=neutral (no sig)
Received: from 127.0.0.1 (EHLO mail-gw0-f47.google.com) (74.125.83.47)
by mta1066.mail.ac4.yahoo.com with SMTP; Wed, 26 May 2010 11:38:12 -0700
Received: by mail-gw0-f47.google.com with SMTP id 15so2437462gwb.20
for <bob_jeff@yahoo.com>; Wed, 26 May 2010 11:38:12 -0700 (PDT)
MIME-Version: 1.0
Received: by 10.231.120.19 with SMTP id b19mr7599387ibr.82.1274899092246; Wed,
26 May 2010 11:38:12 -0700 (PDT)
Received: by 10.231.32.5 with HTTP; Wed, 26 May 2010 11:38:12 -0700 (PDT)
Date: Wed, 26 May 2010 11:38:12 -0700
Message-ID: <AANLkTinhNblWzVPIMCulHZw9DWJUlumWxZYfCIoVsbox@mai l.gmail.com>
Subject: test email from google
From: Jeff Bob <jeff.bob@jeffbob.com>
To: bob_jeff@yahoo.com
Content-Type: multipart/alternative; boundary=00163646d57a84c6e30487839337
Content-Length: 270


Here's the header from from the Outlook email:

From Jeff Bob Wed May 26 18:38:37 2010
X-Apparently-To: bob_jeff@yahoo.com via 66.196.100.97; Wed, 26 May 2010 11:38:40 -0700
Return-Path: <jeff.bob@jeffbob.com>
Received-SPF: neutral (mta120.mail.sp2.yahoo.com: domain of jeff.bob@jeffbob.com is neutral about designating 209.85.160.173 as permitted sender)


X-YMailISG: un2gwrscZAoOSPvXSRFeZqzKsDxNfiHcjDmmEdYc_Mei94ZOOF BTQ5k2I5muxWaulQUYw0D8hNSRpb93BcFz3bN1LT7y_jYgn5w7 sHLqSd1bnZXTq6ePG94DRvgBVHazM4ke9THbp88R4XHyqRzNCw WNEgW8h0RmeLS9sI340ZzP69hslSlewr46.0K.oGRj8jYYmkFx xW0qOj_KMSO0pDH09afbgsksiwWRNCS5lq2MoOxpAMsgNqMfyG lypMPVPxy95aqh0fb9g0bV_v1Rlrgwa7zzoLAztETm9REjuAXf pb4Zs65xp9rXAqRsU8o_0ddBiBAAaTC0oCBvGAq2m_qms2vnls j_mkCuRY5jdbrVcYk6jGHd3euSWgV7f_MFof3TvrXrCuUVZkz9 lLNOaTkdDNeLRxrg9LYrjYoAHJ9cRflMJZesyH4hlejySuaqED 8Ek0CNWfCuDEWIYBWQzZOZDgbTg7oosruOpOavYp2UJm5lbUif hs3UmYsAHN_PLMJ.jz_RcQff6YC9gEzTh065qO_CiJic5lpZny GzJsrCwLDtHOA6n9O21Jeet3lnHStPhq1wKsBh4wje9xvrBsGk _wNTjgHCe1dNWvwyoxJsggCHljiLqTQY
X-Originating-IP: [209.85.160.173]
Authentication-Results: mta120.mail.sp2.yahoo.com from=jeffbob.com; domainkeys=neutral (no sig); from=jeffbob.com; dkim=neutral (no sig)
Received: from 127.0.0.1 (EHLO mail-gy0-f173.google.com) (209.85.160.173)
by mta120.mail.sp2.yahoo.com with SMTP; Wed, 26 May 2010 11:38:39 -0700
Received: by mail-gy0-f173.google.com with SMTP id 5so2918489gyd.32
for <bob_jeff@yahoo.com>; Wed, 26 May 2010 11:38:38 -0700 (PDT)
Received: by 10.231.149.12 with SMTP id r12mr3145588ibv.57.1274899118528; Wed,
26 May 2010 11:38:38 -0700 (PDT)
From: Jeff Bob <jeff.bob@jeffbob.com>
MIME-Version: 1.0
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: Acr9AqeMsvoIbmxcQ8Gxe/9LHUP8oQ==
Date: Wed, 26 May 2010 11:38:37 -0700
Message-ID: <a0032c41f57e77d3560de1b63dba92c5@mail.gmail.com >
Subject: Test email from Outlook
To: bob_jeff@yahoo.com
Content-Type: multipart/alternative; boundary=0016e645b942159a18048783953c
Content-Length: 1848

aquabob,

When you send from your Outlook client it may be trying to relay off a different authoritative mail server. This could cause your mail to end up in their spam folder since you are sending from an autoritatve mail server that is not your own.

Setting up and SPF Record should resolve the trouble you are experiencing. You may want to get in contact with whoever hosts your email and domain in regards to setting up an SPF Record.

Hope this helps.

Mophead