sukh

x I agree but it's down to the company if they want to send via TLS. There 10,000 companies I know who still use SMTP without TLS. Most finance sectors do as its a requirement but many O365 customers still don't.

Potential, only if you're concerned data not being sent via TLS. If you are then I would work on the issue and enforce TLS.

what excht version & post the event. Does it start at all then stop ot simple doesn't start?

I'd look at protocol logging as mentioned & try opportunistic tls for the outbound connector.

autoD maybe an issue but that would only be during startup. if you're saying outlook is online & connected as the inbox takes time to update that is different. did you test with online mode?

wild certs are supported with sp3 was an old issue pre sp3. thr hcw wouldn't complete if cert was an issue.

can you post your outbound connector on o365 can you also up logging on hybrid o365 connector (receive) & see if a connection is being made and the status. I.e protocol logging

you shouldn't have to do that. The hcw does it all for you. I assume you have sp3 on hybrid server? when you send do you get an ndr? where iz it queued? check trace on o365?

what doesn't work? did the hcw complete?

are you talking about exchange here or sp?

just tell them to send you an email and check the MH, it's typically the external ip of the firewall if they aren't exposing exch, either way MH will show.

only internal emails are slow? online mode instant?

when you run the HCW it will create connectors for mailflow. test.

remove the smart host on 2003 if you want all outbound email to go via the 2010 connecter, that should do it.

You need a number of configs, to help prevent spam. 1. Have you setup SPF records? 2. What agents have you got enabled?

How to install Microsoft Anti Spam Agents on Exchange 2007

No, you should have a direct connection so that their Exch server can send to yours, thus, enter their external Exch server IP. Understanding Message Size Limits: Exchange 2010 Help

1. Have you read the privacy data for O365 and how serious this is taken? Some people just hear things and repeat things. If you query and ask what exactly are the concerns around privacy? And what concerns they have for O365 privacy? 2. What issues? Related to email or issues around other MSFT products? I wouldn't combine other issues with O365. 3. Once upon the time, the college didn't have email, nothing wrong with trying something new. To be honest, it's not like O365 is new and they are a Beta customer. There's millions of customer on O365. From what they have told you, I don't see any reason, just excuses or someone who clearly doesn't know what they're talking about.

What exactly are their concerns?

sorted?

sorted?

you can login from anywhere as long as you have a Internet connection. if school network is down then you can still login. unless you have ha for exch then you're better off with o365. in fact why would you want additional costs for email on prem.

what happened? have you tried a different browser on internal network?

first make sure you have tw latest cu & patch outlook & office. can you then check your cas server application logs. cached mode v online mode? what if you click in address book? results? Then drop down & select all users. .results?

I suspect this to. Can we check this out ? Maybe a remote session? PM me.