Problems migrating Gmail to Outlook.com using Outlook 2010

Posted on 2012-12-25
Medium Priority
Last Modified: 2014-11-12
Merry Christmas,

Scenario: User has an above-average GMAIL account (4,000+ contacts, 11,000+ calendar items) with 1.2 GB of e-mails in multiple folders. The User has a Notebook where Outlook 2010 is used with multiple profiles including one for the GMAIL account; has an iPhone and an iPad and is getting a desktop a the office. On the notebook a program from Google to sync Calendar was installed by the user to sync calendar items with Outlook.
The ultimate GOAL is for the user to have access to ALL items, e-mail, contacts and calendars from all 4 devices.

User wants to achieve this by using an Outlook.com account (I am not going to discuss the way or try to find another solution). We have done that many times and have worked like a charm: using the Hotmail/Outlook connector in the PC devices and creating the Oulook.com as an Exchange account on the mobile devices. It just worked; till now.

The problem we are having is two-fold: Limited Connectivity messages on Outlook and Send/Receive errors (and slowness) with Sync Issues in the respective folder. Most of them are like this:
17:53:45 Synchronization error.
17:53:45 Error with Send/Receive.
17:53:45 There was an error synchronizing your folder hierarchy.The network connection is unavailable or interrupted. Please try again later.
We are using the latest 32-bit connector and we have use two different methods to copy the data from the PST file used by the GMAIL account: we have copied items and we have also IMPORT items from the GMAIL PST file while not in use.

Read few post from frustrated users like us with no apparent solution and some coming from GMAIL as well.

So, I wonder if anyone in EE has had this experience before and what suggestions maybe available for us.

Thanks in advance.
PS: Please do not point to Network connectivity issues as all devices can do any other network-based activities with no problems.
Question by:phermi
LVL 31

Accepted Solution

Frosty555 earned 1500 total points
ID: 38720722
IMHO, You're probably not doing anything wrong, especially if you've done this before. I think you're just bumping your head on the systemic issues with using sync services to try and make email work.

When I run into this situation I usually give my users the following lecture:

Gmail and Outlook don't mix. Gmail is designed to be used in www.gmail.com. Outlook is designed to be used with Exchange Server. Period.

Google claims some amount of support for Outlook, and some users have modest success when the accounts are small. But sync utilities are inherently flaky, especially when you scale up the size of the mailboxes. Why? Because Outlook is massively complicated and it is designed with only ONE server technology in mind - Microsoft Exchange.

If the user intends on sticking with Gmail/Google Apps, they should be going to www.gmail.com on their laptops or PCs to access their mail. No exceptions. There's lots of benefits to doing it this way - obviously you can access your mailbox instantly from any computer, no syncing necessary. But the web interface is actually pretty sleek once you get used to it and you can be pretty productive in it.

If they complain "But I like Outlook! I insist on using Outlook!", I tell them it's time to get Microsoft Exchange Server, since that's the back-end technology Outlook is designed to use. *Everything* else is a cludge and you're trying to stick a square peg in a round hole.

If they cannot afford an on-premises server, there are hosted Exchange solutions out there. Many web hosts provide it for a fee. Microsoft themselves actually provides an affordable hosted Exchange service. They change the name of it every once in a while but it is Office 365 / Microsoft Exchange Online.

A Hosted Exchange solution should NOT require any kind of plugin or connector to work with Outlook.

This means things like Hotmail.com, Outlook.com which require "connectors" to work are NOT Exchange server. Similarly things like Google Apps for Outlook, Kerio, MDaemon, Intellisync, Companionlink and various other third party mailservers and "sync" utilities all require Plugins and Connectors to work in Outlook. They will suffer from the same problems you're experiencing now - flakiness, strange behavior and slow performance. When users run into these issues, you can't do much to help them other than fiddle around until it works.
LVL 15

Expert Comment

by:Allen Falcon
ID: 38721203
Given that you can provide access to Gmail and other email accounts through Gmail on all of the devices mentioned, why migrate to Outlook.com at all?  Why not use Gmail as the email service?

Author Comment

ID: 38721644

Thanks for your reply. as refreshing as it can be, I have to solve the current challenges and they are now reduce to SEND/RECEIVE errors and LIMITED CONNECTIVITY.

The Limited Connectivity has been present on the User's office network but to my surprise it also happened from my network.

The SEND/RECEIVE are usually like this:

11:58:54 Synchronizer Version 14.0.6123
11:58:54 Synchronizing Mailbox user@outlook.com'
11:59:58 Network operation failed

11:59:58 Synchronization error.
11:59:58 Folder Collection Sync Key: 0{6ac5d96d-396a-47f1-b541-7983a663b2a5}1
11:59:58 Message Collection Sync Key: 0{8f2d70f5-2fd2-4243-9af7-9ac6e92bdfd9}26
11:59:58 Error with Send/Receive.
11:59:58 There was an error synchronizing your folder hierarchy.The network connection is unavailable or interrupted. Please try again later.
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Author Comment

ID: 38722039

I think you missunderstood me. I am not planning to use GMAIL inside of MS Outlook; I am planning to move Gmail content in OUTLOOK.COM so that I can use the OUTLOOK.COM account inside of MS Outlook.
LVL 15

Expert Comment

by:Allen Falcon
ID: 38722055
If the ultimate goal is to have the user access the account from all 4 devices, you can do this with Gmail.  You can also use Gmail to POP into any other accounts he has.

Why do the move?

Author Comment

ID: 38722073

Really? Please provide details of how to access CALENDAR, NOTES and CONTACTS via POP or even via IMAP fro GMAIL from Outlook.

Once you have tat done, tell me how to do exactly the same from iDevices.

Besides, I did nto ask you or anyone else HOW TO STAY in Google. So if you do not have an answer to my question, just stay out of it.
LVL 15

Expert Comment

by:Allen Falcon
ID: 38722371

I am trying to understand the requirements.  As you know, understanding requirements is the best path to the best solution.

So ....

The best way to migrate data OUT of Gmail is to use Outlook to generate a PST file, or to use the snapshot tool from Backupify to extract all of the data.  From there, you can import into just about anything.  Cal/Contacts must be exported to CSV separately if you export via Outlook connected using IMAP or POP.  Snapshot will pull calendar and contact info as well as email.

As an alternative (and the reason for my question) ...

With Google Apps for Business (paid account), you can use MAPI protocols via the Google Apps Sync for MS Outlook (GASMO) add-in to connect Outlook fully to Google Apps (outlook will think Gapps is an exchange server).   For you iDevices, integration is native.  You can use ActiveSync for all data, or IMAP for Email and Google Sync for Calendars and Contacts.

This does require a Google Apps for Business ($50 per user per year) account.

Once configured, GAFB can POP email from up to 5 other services into a single, or separate inboxes -- all will sync with all devices.

I am assuming, since your did not say otherwise, that your user is a business or would be willing to pay a small amount for a bullet-proof service and solution.  If not, if the user only wants free, then they shouldn't stay with Gmail as the cal/contact sync is no longer available for free users.

Author Comment

ID: 38722540

I see you did not provide as to how IMAP Calendar and Contacts ....

Regarding requirements, there are NONE as I am not looking for an Email solution but to causes of the very concrete errors I am having. I've in IT for 35+ years, so you know, I know about a bit about requirements.

Few things, first, User is personal not a business (actually someone starting back in the work force as independent contractor) who decided on its own to consolidate years of OST from Exchange inboxes into FREE GMAIL. User is familiar with Outlook and wants to use the data from it.

Therefore, there is no DOMAIN to use in Backupify  Snapshot. If the User will be willing to pay at Business Gmail, I will put it on Office 365 instead, as Exchange is pretty bullet-proof too.

As much a I;d love to chat, if you do not have an answer to my very specific situation, feel free not to post anymore.

Expert Comment

ID: 38722963
Hello Phermi,

Please follow guidelines mentioned in following articles:-

1. http://blogs.office.com/b/microsoft-outlook/archive/2012/08/09/upgrade-from-gmail-to-outlook-com-in-5-easy-steps.aspx
2. http://www.howtogeek.com/howto/17248/set-up-gmail-imap-in-outlook-2010/

Hope that it will sort out issue.

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Author Comment

ID: 38723597

I do not want to add Gmail to MS Outlook as that is what the User already has and it does not provide the solution. That is what your second link is all about.

The objective of my post was to search the EE community for people that have had similar situations and errors I've found and hear about their solutions or workarounds if any.

Regarding the first link you provided, which is more in line to what I have done, I discarded the Contact Linking because after waiting long enough, I never really saw the contacts INSIDE of Outlook.com reachable to MS Outlook. Maybe something went wrong, but the only way to see the contacts was by logging into Outlook.com / People.

On the bright side, that link mentions one tool that is new for me, Trueswitch. I will give it a try.

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