Connection between Office 365 and Outlook dropping out

[dezt]

I've been trialling Office 365 for about a month now before we roll it out to all staff, the OWA works great, so good we have migrated the students from our in house exchange 2003 and they are using it with ease.

I have come across a small problem though, when I have set up outlook to connect to my office 365 account, it works for a while then I get a yellow exclamation mark in the bottom right corner and instead of saying "Connected to Exchange", it says "Trying to connect" I thought it was because of the encrypt connection to exchange setting, but have just noticed even when this is unticked the problem still occurs.

I have seen 1 other thread on here about this, but the OP didn't get any replies, here is a link to the original post Office 365 connection problems...

Has anyone come across this problem? does anyone know how to fix it?

[ZeroHour]

I suppose the first question is what do you route through to get to the net filtering/firewall wise?

[sukh]

Use the Exch RCA and see what that reports and post the results.

https://www.testexchangeconnectivity.com/Default.aspx

[EduTech]

I have not seen this happen yet in the deployments that I have done, but it would be interesting to know what kind of connection you have, (Filtering? Proxy? etc.) using the link that Sukh provided ensure that all your external connectivity is okay.

What kind of internet connection do you have btw?

Thanks,
James.

[dezt]

From what I can see in that, https for my autodiscover is not enabled. Apart from hat I'm not too sure

[dezt]

A bit of additional info, when I run the autodiscover tests, sometimes it times out and I have to run the test again.

[EduTech]

I recommend you remove your email address from the above posts mate, maybe upload screenshots and blur out your personal information sir.

Upload the images, with all tests expanded.

--

I can see that you the correct CNAME DNS Entry for autodiscover point to autodiscover.outlook.com

You are not using a Hybrid Deployment are you?

James.

[sukh]

Did you create all the appropioate records? It seems like the SRV for autodiscover worked?

Did you a CNAME for autodiscover?

External DNS Records

Use a CNAME Record to Enable Outlook to Connect

[sukh]

What sort of an internet connection do you have?

Can you monitor the internet link? For any packet loss?

[dezt]

Cheers for that @EduTech, I'm on the ipad at home, I'll upload screenshots in the morning, I'm using a hybrid at the moment, as soon as everything works with outlook, I'll be moving across to a full office 365 solution, we have the kids on it at the moment, I just need to get the mx records setup when all the staff are migrated across.

Is that the right way to do it, migrate mailboxes to office 365, let staff connect to OWA while mx records are changed at LEA to point to office 365 and then switch off the exchange server. Please tell me if that's not the recommended route.

[dezt]

@sukh I did get the lea to create a CNAME record for autodiscover, it took a few phone calls, but when I do a nslookup on it, it points to autodiscover.outlook.com like it should do.

I'm on the CLEO network for broadband, so it's whatever is provided by BTOneconnect ltd.

[EduTech]

Cheers for that @EduTech, I'm on the ipad at home, I'll upload screenshots in the morning, I'm using a hybrid at the moment, as soon as everything works with outlook, I'll be moving across to a full office 365 solution, we have the kids on it at the moment, I just need to get the mx records setup when all the staff are migrated across.

Is that the right way to do it, migrate mailboxes to office 365, let staff connect to OWA while mx records are changed at LEA to point to office 365 and then switch off the exchange server. Please tell me if that's not the recommended route.

If you have a Hybrid Deployment the External Autodiscover Record should point to the External IP Address of your Exchange 2010 Hybrid Server. The Hybrid Server is then clever enough to know when a mailbox on Exchange Online or OnPrem and then re-directs the request accordingly. (or at least that is how i have always done it)

Regards,
James.

[EduTech]

@sukh I did get the lea to create a CNAME record for autodiscover, it took a few phone calls, but when I do a nslookup on it, it points to autodiscover.outlook.com like it should do.

I'm on the CLEO network for broadband, so it's whatever is provided by BTOneconnect ltd.

The MX Records should stay pointing to your OnPrem at the moment, it will handle the mailflow and then when you have your mailboxes moved over you can then point the MX Records to Exchange Online.

The same goes for the autodiscover record, this should point to OnPrem and then when you have migrated over you should then create the CNAME and point it to autodiscover.outlook.com.

Regards,
James.

[dezt]

I think I have an issue then, I don't have an exchange 2010 box, mine is an exchange 2003, should I migrate the mailboxes over the Christmas holidays and get the mx records changed then?

[dezt]

@EduTech looking at your last post, my problem is where the autodiscover is pointing to, it looks like I have a setup that points both to the exchange server we have, and to autodiscover.outlook.com, that may be confusing things.