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Alternate SMTP Server in Office 365

Posted on 2014-03-06
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Last Modified: 2015-07-26
Good Morning,

I have a client that I recently migrated from SBS 2003 to Windows Server Essentials 2012/Office 365 and it is all working quite well.

One minor thing however that annoys them slightly is the slow sending of emails. They only have a slow upload speed on their ADSL 2+ connection (512 Kbps) and as they are solicitors they often handle quite large scanned documents.

This means that some messages tend to stay in the Outbox for up to 1 or 2 minutes which frustrates the CEO of the company (which means I get the agitated phone call)

With their old setup on SBS 2003, the message left the outbox pretty much instantaneously on route to the on premises Exchange 2003 Server.

What I would like to do is setup a secure SMTP relay on the SBS 2012 Essentials Server (already done and tested OK) and route outgoing email through this server instead of the Office 365 SMTP Server

Don't know if this is possible, searches on the web have come up blank so far.

It's a minor problem, but it's causing me major grief

Anyone have any ideas?

Gerald
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Question by:gezzam25
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Expert Comment

by:Brad Bouchard
ID: 39910959
I'll save you at least some time and headache in telling you that this cannot, nor will it ever, happen.  Microsoft will never allow any relaying of any kind.  I've tried with with things as small as scanners that scan to email, or a program that needed alerting setup and an SMTP server to send through, and even those didn't work.  MS themselves will tell you that this isn't allowed.
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by:N-W
ID: 39911289
If they're using Exchange with O365 (rather than POP3/IMAP), then the users aren't actually using SMTP to send emails to the O365 server, so what you want to do will be impossible.

You best option would be either to upgrade their Internet connection to a faster link or move to on-premise Exchange. Unfortunately the Internet connection speed is always a major factor that's over-looked when choosing between cloud vs on-premise services.
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by:Cliff Galiher
ID: 39911445
I agree with N-W, but I'll expand a bit. It sounds like you are trying to play a "shell game" with the client.

On SBS 2003, on that same connection, the email would leave the outbox quickly to the on-premises exchange server, and then would sit in the exchange server's outgoing queue for the same 2-3 minutes as it send to the destination server.

If you did manage to set up an outgoing SMTP relay on your Essentials server, it'd be the exact same thing.

The point being; the message isn't leaving the LAN for several minutes. But with Office 365, the GUI just makes that delay more apparent. It wouldn't actually *improve* or even change anything by setting up an SMTP relay...except make things more complex and provide a false perception of faster sending.

The solution is explain the situation to your client...or upgrade the connection.

----

Now there is one caveat to the above. One user sending to another *on the same Exchange server* would be faster with on-premises Exchange...for example your old 2003 network. However setting up an SMTP relay would *not* improve that, because the message would still be going out and coming back in.

But I'd argue even with Exchange (or SBS) 2003, that isn't the optimal way to send large files. It is actually quite impractical. A file server would make more sense, and you simply email the link.

You can extend this premise even now. I'd argue that if these attachments are large, it is best not to email them. Recipients can get angry if they get a large attachment that slows down their whole send and receive. And in the era of mobile phones and data caps, that can be *very* annoying. Using a service to share files and email links is still preferred, even with external clients.  Dropbox has business accounts that allow this, as does box.net.  And, of course, OneDrive For Business recently added this option as well, and that is also included with Office 365, so you already have this capability. Just a matter of picking the service that has the best features for your use.  Any which way, it'd also resolve the 1 to 2 minute outbox issue. And be more friendly to the recipients in the process. Win/Win. Just a matter of changing habits and education.

-Cliff
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Author Comment

by:gezzam25
ID: 39911477
"It sounds like you are trying to play a "shell game" with the client."

That's exactly what I was trying to do and he was well aware that this workaround, if possible, was a patch fix.

"You can extend this premise even now. I'd argue that if these attachments are large, it is best not to email them. Recipients can get angry if they get a large attachment that slows down their whole send and receive. And in the era of mobile phones and data caps, that can be *very* annoying. Using a service to share files and email links is still preferred, even with external clients.  Dropbox has business accounts that allow this, as does box.net.  And, of course, OneDrive For Business recently added this option as well, and that is also included with Office 365, so you already have this capability. Just a matter of picking the service that has the best features for your use.  Any which way, it'd also resolve the 1 to 2 minute outbox issue. And be more friendly to the recipients in the process. Win/Win. Just a matter of changing habits and education."

Easier said than done, the clients conveyancing software uses mail merge to create the documents and this software then converts them to PDF. From this software you then email the said document. Also, my client has been doing things this way for years and simply doesn't want to change. When he sends the documents, he immediately goes to sent items and prints them out as hard copy for his records (he has a room full of hard copy files from over 20 years of being in business).  Thus the issue of the mail remaining in the outbox for a minute or so. He is in his 50's and it's the way he works and no magical software is going to change his mind. (You should have seen the grief I got when we upgraded from WinXP and Office 2003 to Win7 and Office 2010).

I thought this would work OK, but I was terribly mistaken.

 Just a matter of changing habits and education is not going to be the solution.

I tried to explain all the above (which makes perfect sense to me) to the client. His succinct response was "I don't want to hear problems, I want to hear solutions"

So, the solution is that we are blowing away Server Essentials and Office365 and installing SBS 2011 Standard at his cost and he doesn't mind one little bit.....

Sometimes what we know is best and what the client wants are two totally opposite things and we have to try to bend the rules to accommodate their whims. My idea obviously was never going to work.

Win/Win for him, but a long night next Friday for me :-)
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Cliff Galiher earned 500 total points
ID: 39911568
Since you already have essentials, may I at least suggest doing a OS running 2012 Standard and exchange 2013? Essentials will integrate with it just as well as it does O365, and you don't have to scrap tour existing Active Directory domain or struggle with migrating files and resetting ACLs. A server powerful enough to run SBS 2011 would run Hyper-V with two VMs just as easily. I'd humbly suggest this is a more forward-looking solution.
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Author Comment

by:gezzam25
ID: 39911624
It's only a 5 user network, just backup PST's and create new AD users. Only one internal conveyancing application and a few GPO's to redo. Oh and one multifunction printer. I'll have it done in 4 hours or so.

It's why I went Essentials/O365 route in the first place. Wanted to simplify it all. It wasn't until I discovered the outbox issue that we realised it was the wrong option. I'll just replicate the SBS2003 system configuration he had on an SBS2011 system. I wanted to do the SMTP thing so I didn't have to buy and install SBS Standard.

He's been a client since SBS 4.5 days and I never knew that's how he worked. Well I do now, it proves even after knowing a business owner for 12 years you don't know everything about them. Lol...

Thanks for the ideas though

Gerald
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