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Old 03-18-2013, 11:21 PM   #1
Join Date: Oct 2011
Posts: 6
Question Outlook 2011 - can't send to Gmail?

Hi all,

Outlook 2011 has stopped users from altering or deleting additional headers... including ones automatically imported from Entourage 2008. Is there any manual way to remove these?

Here's my problem, in 3x dot points:

~ Before I started at work, my users used to use Entourage 2008. This was connected to Gmail IMAP accounts, and they'd use Entourage's additional headers to specify "From:" as "user@company.com", which would (mostly) mark outgoing mail with the company's FQDN.

~ Just when I started, management pushed to move all staff to Office 2011. We used Outlook 2011's inbuilt "Import" feature to import staff profiles - including profile-specific things (like groups of contacts, and recently-typed recipient addresses). This worked fine. In reality, we've only moved about 60% of the company to Outlook '11, as management were the only ones really pushing for it - most users didn't care.

~ Now, we've implemented a new, internally hosted IMAP server. Outlook 2011 connects to the new account - and mostly works, but users can't send to Gmail addresses. Messages are going out with duplicate From: headers. Gmail still completes SPF checks on From: header quantities, it counts our headers as >1, and bounces the message with:

>: host
>> said: 550-5.7.1 [xxx.yyy.zzz.ip 11] Our system has detected
>>that this message is 550-5.7.1 not RFC 2822 compliant. To reduce the amount
>>of spam sent to Gmail, 550-5.7.1 this message has been blocked. Please
>>review 5.7.1 RFC 2822 specifications for more information.
>>cg2si14794008pbc.244 gsmtp (in reply to end of DATA command)

It's Outlook specific - the Entourage (or webmail) users don't get this.

Is there some way of manually changing the headers of an imported profile?
Alternatively, how may group contacts/recently-typed addresses/etc. be backed up and comprehensively restored into a new one?

Thanks in advance,


Last edited by scottmusician; 03-18-2013 at 11:24 PM.
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Old 03-20-2013, 07:41 PM   #2
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Join Date: Jan 2007
Location: Oregon
Posts: 618
Outlook 2011 does not support headers but can import headers and some other preferences from Entourage. However once imported there is no way to delete or change these settings.
Diane Ross,
Office Mac Help
Need Help for Mac
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Old 03-22-2013, 10:01 PM   #3
steve hoge
Join Date: Mar 2013
Posts: 3
I just recently - last few weeks - started running into this problem with sending mail through Gmail's servers using Outlook (14.3.1), and I was totally flummoxed about what aspect of RFC2822 (a VAST specification) I was violating.

I'm trying to figure out whether Gmail's servers have become more stringent or whether Outlook 14.3.1 is doing something new that the previous version wasn't. Any clue? I don't particularly mind reverting to a previous version of Outlook if there was some change in its behavior.
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Old 03-25-2013, 11:42 PM   #4
Join Date: Oct 2011
Posts: 6
Thanks for the replies! I'm glad i'm not going completely crazy.

So, Outlook has imported and cemented these settings somewhere into it's profile. I can create a new profile for each effected user, but they'll lose whatever Outlook-specific data they have which isn't stored on the IMAP server. So far, I see this data falling into two categories:

a) Locally stored groups of contacts
b) Recently-typed addresses that weren't 'saved', per se, into the address book

I can always re-type the blast addresses if needed (it's only about 10 users). But any thoughts on how to comprehensively export+import outlook's contact groups?

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Old 04-07-2013, 08:18 PM   #5
Join Date: Oct 2011
Posts: 6
What a horrible problem. After months of looking at this, I've managed to work out how to fix permanently. Here's how:

The Outlook 2011 profile needs to be rebuilt for each effected user. Doing it via the following method will ensure that no extraneous data will be lost. Note that you will need the account credentials, including server info, and the end user's username and password. Fortunately, it's pretty straightforward:

- Open Outlook
- If the user has any mail "Folders on my computer" (ie. locally-stored mail), then export these to an archive using "Export... " from the Outlook menu
- Close Outlook
- Navigate to the User's "~/Documents/Microsoft User Data" folder. Rename the "Outlook 2011 Identities" folder to "Outlook 2011 Identities Old". From the "Outlook 2011 Identities Old" folder, copy the "MeContact.plist" file, and paste it into the new "Outlook 2011 Identities" location.

- Open Outlook again. It won't be able to see any pre-configured profiles, so it'll make a new "Outlook 2011 Identities" folder.
- Re-connect outlook to the user's mailbox by creating a new account. After Outlook connects to the account, it will automatically start "syncing" to create a cache of each folder. Instead of leaving the program to complete this sync, for now please close Outlook as soon as the account is configured.
- Navigate to your "Outlook 2011 Identities Old" folder. Click on the Main identity (or most recently modified Identity folder), and then on the "Data Records" subfolder. From this directory, hold the Command key and select all of the following subfolders:

Categories, Contacts, Events, Preferences, Recent Addresses, Saved Searches, Schedules, Signature Attachments, Signatures, Tasks, UIDs.

- Choose "copy" from the Edit menu. Head to the new "Outlook 2011 Identities" Folder, and copy these subfolders into the appropriate "Data Records" folder within the new identity, overwriting any existing folders.

- Start Outlook again. It will likely want to do a database rebuild, but this shouldn't take very long as the new profile is basically empty. Once it's completed and outlook has started, quit Outlook again.

- Head back to your "Outlook 2011 Identities Old" Folder, and into the main identity. This time, copy the following single files from the identity's root folder:

Rules, Mailing Lists, Signatures

Paste these files into the corresponding place in your new identity.

- Finally, startup Outlook. The new profile should successfully be rebuilt, with all contact groups/recent searches/etc. all as they were. You might want to send a test email to yourself, and inspect the headers to ensure that you now only have 1x "From" header. Outlook will say "Sync Pending" for a while, and it will need to synchronize all folders - including the Inbox and Sent Items, which can take some time depending on the size of your mailbox and your network speed. Fortunately, Outlook does seem better at automatically syncing all folders than Entourage (although it could be just me) - you shouldn't need to click on every single folder in order to start caching process.

Now you have a happy Outlook. It might take Gmail (or other recipients) a few days for their systems to work out that you've become RFC 2822 compliant, but they'll work it out soon.


You can further increase the "trustworthyness" of your domain's emails, by adding an SPF record to your DNS. Before doing this, ensure that all email accounts actually send mail through your SMTP server - as accounts still using legacy "from:" headers to forge SMTP origins will no longer work once this has happened.

Putting in an SPF record is good practice and will decrease the likelyhood of spammers exploiting your domain. Nick Wilsdon's page on SPF records explains it really well - do a google search and hopefully it'll come up (i tried posting the link by the forum software is stopping me)

It's simple to implement: in your dns records, add a new TXT record, with an entry like this:

v=spf1 a mx ~all

So the command to add this (ie. the record you would end up in with in your DNS zone) will be similar to:

yourdomain.com. IN TXT "v=spf1 a mx ~all"
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Old 04-12-2013, 08:25 PM   #6
steve hoge
Join Date: Mar 2013
Posts: 3
Aren't the special header specifications imported from Entourage stored PER ACCOUNT (under the Options tab) rather than PER IDENTITY? From that I would infer that simply deleting and then manually recreating the account would be enough to remove extraneous headers that were inherited from an Entourage import.
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Old 04-13-2013, 02:54 PM   #7
steve hoge
Join Date: Mar 2013
Posts: 3
This indeed appears to be an issue with accounts that were originally created in Entourage and migrated to Outlook.

I was able to solve this by simply deleting the specific Gmail POP Account in Outlook - which had been migrated from Entourage - and then recreating it from scratch - a 5 minute operation. No Export/Import cycle of User Identity data was required (which is buggy in Outlook anyway.)

Recreating a fresh Account eliminated the multiple "From:" headers - as reflected back in the RFC2822 error message returned from Gmail's servers - which had slightly different formats and which were apparently triggering Gmail's spam filters.

Looking at the interpretation of those headers in Gmail's web interface showed that offending emails had "Reply-to" headers that were different from the initial "From:" header. The "Reply-to" headers disappeared after the Outlook Account was recreated by hand. I know for a fact that my original Entourage Account settings from which this was migrated had an additional "Reply-to" header specified - which as Diane has pointed out are embedded but inaccessible inside Outlook's Account settings.
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