Combining Gmail and Exchange 2010

Hi Experts,

Is there a way to use Gmail and Exchange SBS 2011 (2010) and effectively use both systems and keep them synchronised?
If I can avoid the unreliable POP3 connector from SBS I'd be happy.
Maybe use SBS as primary and a second MX to Gmail , but how do I keep mailboxes in Sync.
Any ideas , suggestions anyone?
Have any of you used  this, in what format, any pit falls?
This client already has Gmail setup with their own domain but I am installing a new SBS for them this week.
Thanks,
Olaf
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Olaf De CeusterAsked:
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Frosty555Commented:
By Gmail, I'm assuming you mean they are using a paid edition of Google Apps for Business.

The mail for each user's mailbox must be stored somewhere. Either it is stored in on Google's servers (Mailbox is in Google Apps), or it is stored on the SBS 2011 server (Mailbox is in Exchange). It can't exist in both places at the same time, synchronization is not really feasible.

You CAN have a hybrid environment where some users are on one system and some users are on the other. This is useful when you are in mid-migration.

You can configure mail routing on either server. Email arrives on the first server (e.g. Google Apps), and messages destined for a mailbox that doesn't exist gets passed along to to the secondary server (e.g. Exchange Server). Or vice versa.

https://support.google.com/a/answer/96855?hl=en

This is different from having the mail exist in BOTH locations, which is nearly impossible.

Really it depends on what you're trying to accomplish. Which mail system do you intend to use going forward?
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Olaf De CeusterAuthor Commented:
Hi Frosty,

I'd like to use both systems in Sync. Don't really mind which is the primary.
Possible?
Thanks for your input so far.
Olaf
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Frosty555Commented:
Sync? No. Nothing that I would  be comfortable recommending.

You can check out imapsync, which you can run on a server and will sync two IMAP mailboxes. Since Google Apps and Exchange Server both support IMAP, you could potentially use this tool.

http://imapsync.lamiral.info/

But you'd need to manually configure every account, you'd need to possess and store the password for every account, and you'd have to constantly keep the imapsync service up to date with changing passwords. It would be a messy and difficult and a major security hole. But possible? I suppose so.

What are you trying to accomplish? The core problem here isn't so much that you can't sync content between the two services, but WHY you want to do that in the first place?
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Olaf De CeusterAuthor Commented:
Because they used to have their mail with Google apps but now have their own emails server. Some users however like gmail.  So I was hoping to offer both if possible.
I guess I could setup Imap on outlook clients also?
Olaf
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Frosty555Commented:
You could have a hybrid environment like I said in my first comment. Some user's mailboxes are in Google Apps, and the rest are in Exchange Server.

But this is really making more headache than it is worth, and IMHO, I would not offer this as a possible solution to the client, because in the end *you* are going to be the one who has to support it.

It's not uncommon for some users to stubbornly resist change, but the bottom line is your client made the executive decision to move to SBS and Microsoft Exchange. The users do not have a choice anymore. Migrate them, they'll get used to it.

To help smooth things over, migrate the problematic users near the end, after you've got all the kinks out, and make sure you understand the feature parity in Gmail vs Outlook, and sit down with them for a few minutes and show them how to do things to help ease them into the new environment.

For simplicity sake, especially with problematic users, avoid mixing Gmail and Outlook. Google Apps mailboxes should be accessed exclusively via the www.gmail.com interface, and Microsoft Exchange mailboxes should be accessed exclusively using MS Outlook. Keep it simple for them.
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Gareth GudgerCommented:
Agree with Frosty.

One thing I am curious about. Why are you going with SBS 2011? Microsoft has retired this product and will no longer be actively developing it.
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Olaf De CeusterAuthor Commented:
Hi Frosty,

Thanks for the info. I convinced the client to run in house exchange. Rolling out now.
Great advise.

Gareth,

Because its the perfect fit  money wise in countries with bad internet (I am rolling this out in Vanuatu) and I know the product really well.
Cloud here is not an option yet.
If there was a replacement for SBS out there I would happily sell it to my clients. Needs to be an all in house option or a complete hybrid solution for similar money. Do you know of any?
Always very open to opinions/ ideas.

I will leave question open to see if I get anymore comments.

Olaf
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Olaf De CeusterAuthor Commented:
We are using a hybrid solution. The Imap solutions were not working well because when internet drops the sync starts all over again and makes things worse by clogging up the internet connections.
Am using POP (not the SBS pop connector because that does not allow me to keep a copy on the Gmail server) in outlook to download messages into the  users OST file. Primary MX record is pointing at the SBS server, secondary at Gmail. Note that the aim is to get rid of Gmail soon . Otherwise I would have kept the primary MX pointing at Gmail.
Considering  the clients limited bandwidth this works OK.
Please note also that the reason I ran their own email server was that 50-70% of email send is destined for colleagues in same office. By eliminating this internet usage (emails are locally send) I have improved their general browsing experiences.
Thanks all for your input.
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