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gmail "sent mail" folder not synchronizing with outlook 2016 "sent mail" folder

Posted on 2016-10-18
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Last Modified: 2016-10-27
I installed office 2016 on a computer.

I configured Outlook to a gmail account manually via IMAP. I couldn't let autodiscover configure the account because it is their domain name, not gmail.com

Everything seemed to work fine until last night I was taking one last look in outlook and noticed that I didn't see  "sent mail" from his iPhone, only sent mail that is from this outlook profile.

When I look on gmail servers I see his iPhone sent mail along with Outlook sent mail.

Apparently the reason I see sent mail in outlook is because I haven't yet unchecked "do not save copies of sent items" When I do check that in the settings of outlook it doesn't even save as sent mail, much less uploading it to the server.

I realize that for gmail I need to check this box in order to not have duplicates in the sent mail folder (1 that gmail automatically creates and 1 that outlook would puts up there when "do not save copies of sent items" isn't checked.

Looking at the synchronization logs I see that "sent mail" shows local changes are synced online to the server but I don't see server changes to the syncing from "sent mail" to Outlook. There is a sync error following that. I'm guessing that's the problem.
Sync log is below

One other thing, has anyone every seen someone "root" an imap account in a users directory?
The reason there is a "'C:\Users\somebody\Documents\OUTLOOK" folder is that the user previously was using office 2010 and they rooted the Imap account there. Which was ok for 2010 when you could chose your sent items and deleted items folder.

Other that that, once I'm sure I have full access to the machine again I will try this suggestion https://www.experts-exchange.com/questions/26414163/Exchange-2010-Error-synchronizing-folder.html ( to see if it applies, although I can't imagine since other folders sync.

 

Importance: : Synchronization Log:



20:16:52 Synchronizer Version 16.0.7369.6529
20:16:52 Synchronizing Mailbox 'somebody@somewhere.com'
20:16:52 Synchronizing Hierarchy
20:16:52          1 folder(s) updated in online store
20:16:53 Synchronizing server changes in folder 'Drafts'
20:16:53 Synchronizing server changes in folder 'Inbox'
20:17:05          1 item(s) added to offline folder
20:17:05 Synchronizing server changes in folder '[Gmail]'
20:17:05 Synchronizing server changes in folder 'Sent Messages'
20:17:05 Synchronizing server changes in folder '[Gmail]Drafts'
20:17:06 Synchronizing server changes in folder '[Gmail]Trash'
20:17:06 Synchronizing server changes in folder 'C:\Users\somebody\Documents\OUTLOOK_PST'
20:17:06 Synchronizing server changes in folder 'Deleted Items'
20:17:10 Synchronizing server changes in folder 'Drafts'
20:17:10 Synchronizing server changes in folder 'Experts'
20:17:11 Synchronizing server changes in folder 'Jerry Bachelor Party'
20:17:11 Synchronizing server changes in folder 'Junk Email'
20:17:11 Synchronizing server changes in folder 'Junk E-mail'
20:17:12 Synchronizing server changes in folder 'John Doe Emails'
20:17:12 Synchronizing server changes in folder 'Sent Items'
20:17:13 Synchronizing server changes in folder 'Deleted Messages'
20:17:14 Synchronizing server changes in folder 'DISD'
20:17:14 Synchronizing server changes in folder 'Drafts'
20:17:14 Synchronizing server changes in folder 'Follow up'
20:17:14 Synchronizing server changes in folder 'Junk E-mail'
20:17:15 Synchronizing server changes in folder 'Misc'
20:17:15 Synchronizing server changes in folder 'ND - Send to NetDocuments'
20:17:15 Synchronizing server changes in folder 'Notes'
20:17:15 Synchronizing server changes in folder 'Priority'
20:17:16 Synchronizing local changes in folder 'Sent Mail'
20:17:16          1 item(s) added to online folder
20:17:16          1 item(s) deleted in online folder
20:17:16 Error synchronizing folder
20:17:16              [80040119-20010C01-800408C4-310]
20:17:16              Outlook Data File
20:17:16 Synchronizing server changes in folder 'Trash'
20:17:16 Synchronizing server changes in folder 'Spam'
20:17:17 Done
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Question by:bwierzbicki
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LVL 43

Expert Comment

by:Jackie Man
ID: 41849448
Have you changed “Mailbox Behaviors” items as needed for the "Sent Mailbox" in your iPhone to match the Sent folder on IMAP server?

https://support.sanebox.com/hc/en-us/articles/203094816-iPhone-Setting-up-your-Sent-folder

1. Start at the Home screen and go to Settings

2. Choose “Mail, Contacts, Calendar” and select your IMAP account & Choose the Account (e.g., user@mail.com)

3. Scroll to the bottom, select “Advanced”, and change each of the “Mailbox Behaviors” items as needed (e.g., Choose Sent Mailbox and check "Sent Items")
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Author Comment

by:bwierzbicki
ID: 41850175
Thanks for you answer Jackie Man,
unfortunately that wont solve my issue. The mail from the iPhone is actually making it to the "sent mail" folder, it's just not downloading to Outlook. If I look at gmail server via webmail I see all the sent mail, Outlook (it uploads a sync apparently) I also see what was sent from the persons iPhone, it just doesn't sync to Outlook.
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Expert Comment

by:Jackie Man
ID: 41850266
From MS Outlook 2013 onwards, IMAP account of GMail does not work properly in terms of the messages in sent folder will NOT be synced with GMail sent mail folder.

There is no fix as the communication protocol has changed. Details are in the link below.

http://www.slipstick.com/outlook/outlook-2013-imap-folder/

Apart from the workarounds as stated in the above link, I suggest you to add a rule for outgoing mail that a copy of the sent message will be copied to the sent mail folder of GMail server.
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Author Comment

by:bwierzbicki
ID: 41850529
Hi Jackie Man, thanks again for your comments but I may not be making myself clear.
Outlook is putting the sent items in the correct folder on gmail "sent mail"
the problem is that when outlook Imap folders try to sync from the server DOWN to outlook, it doesn't sync Outlook with what is already on the server, the stuff from the iPhone, which also correctly goes to the sent mail folder on gmail, and also when looking at the iPhone, shows the items that were sent from outlook.

in a nutshell, there is no problem with Outlook populating Gmail sent mail folder
The problem is retrieving from Gmail's sent mail folder.
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Expert Comment

by:Jackie Man
ID: 41850622
So, if you sent a message from GMail, do you see it in Sent Mail folder of MS Outlook 2016?
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Accepted Solution

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Lisa Hendrickson "CallThatGirl" earned 500 total points
ID: 41850747
How many emails are in the sent folder in the Outlook folder? I have seen this before, if a client has over 10,000 or around there, I would move off as much as the client will allow you to a local PST file. Sent can be very finicky on IMAP.

I do IMAP/Gmail clean ups all the time, unless you turn off IMAP in the settings of Gmail --which is not recommended of course with the sent items, it's usually a case of email overload. This can go for any folder too.
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Author Comment

by:bwierzbicki
ID: 41850755
57,772 in sent mail.
I will begin moving these as soon as the client gives permission.
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LVL 6
ID: 41850765
OMGosh yes....move out everything before 2016. That's usually good enough to get the sent back in action.

~Lisa
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Author Comment

by:bwierzbicki
ID: 41852122
Thanks Lisa, I'm waiting to hear back from the user in regards to moving to pst. Looks like it will be a 2 part move, one to some other folder from gmail interface, then syncing that new folder to Outlook IMAP and lastly moving from that IMAP folder to the pst.

Also I was wondering if anyone had a comment on the other part of my question
One other thing, has anyone every seen someone "root" an imap account in a users directory?
 The reason there is a "'C:\Users\somebody\Documents\OUTLOOK" folder is that the user previously was using office 2010 and they rooted the Imap account there. Which was ok for 2010 when you could chose your sent items and deleted items folder, which is what they did with that pst, but it created a weird label in gmail with that path as the label name. I'm just wondering if they were doing it for some obscure reason/solution, or if it was just a mistake by the last person that set up the IMAP profile.
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Expert Comment

by:Jackie Man
ID: 41852150
One other thing, has anyone every seen someone "root" an imap account in a users directory?

"Root" is not supported from Outlook 2013 onwards for GMail.

Anyway, my findings indicate that IMAP GMail account does not work for Sent Mail folder from Outlook 2013 onwards and it is normal that there will only be local sync not server sync for Sent Mail folder.
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Author Comment

by:bwierzbicki
ID: 41852161
Hi Jackie man,

I've seen what you mean in regards to 2013 on not allowing you to select where to put sent, deleted and drafts from outlook but I'm almost certain that along the way I setup a test gmail account/profile on my machine in outlook 2013 and the same gmail account on my iPhone. If memory serves, it worked as expected with sent mail from website, iPhone and Outlook going to the sent mail folder.
I'll re-open that profile, test and report back as soon as I get a chance.
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Expert Comment

by:Jackie Man
ID: 41852191
Test account will work because their is no message inside Sent Mail folder.

In real life situation, it will not work as it is normal to have a few thousand messages already in Sent Mail folder and it will just got stuck if you add IMAP GMail account in MS Outlook 2013 onwards.

http://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_winother/outlook-2013-not-downloading-all-gmail-messages-in/774b3c1c-64ff-420b-a886-642e9401c2e0
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Expert Comment

by:Jackie Man
ID: 41852202
And moving most messages in Sent Mail folder to a local PST file defeats the purpose of setting an IMAP account because you want the messages to be there online when you want to search them.
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LVL 6
ID: 41852212
I agree Jackie Man, but Outlook can only hold so much before it breaks sometimes. Gmail on the browser can hold lots more email. Outlook and esp with IMAP has limitations.

If you move it to a PST, they can still search that folder.
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Expert Comment

by:Jackie Man
ID: 41852213
If you move it to a PST, they can still search that foldery

Yes... If you are using MS Outlook.
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LVL 6
ID: 41852223
And they are, it's in the subject title of this question.
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Author Closing Comment

by:bwierzbicki
ID: 41863068
Turns out it just started working.
Last time I looked the Sent Mail folder had caught up and was functioning as expected. Outlook and iPhone email stored on the server's "sent mail" folder/flag

Jackie Man I appreciate your replies and I've seen the articles that you used as reference in regards to why it wouldn't work with 2013 Outlook and up, but in practical application those articles are deceiving. The gist of what I've seen is that it WILL work, you just don't get to chose your sent and deleted folders anymore. Outlook basically makes it's best guess according to what it gets from the server and you are stuck with it.

I'm not sure why it started working out of the blue, but I am about to move these guys to Office365 so I'm just glad it started working in the interim.

Thanks again
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