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Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Thanks. I'm almost there. Just need to set up this, then my proxy in our DR facility and the SSO portion will be over.

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Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Holy poo poo, after deleting a bunch of corrupted messages out of tha tusers mailbox, the O365 sync finally completed and it's ready to run every 24 hours.

Boss is dragging his feet approving the certificate for ADFS but at least I've got some progress!

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Ok, just a quick question...

So we have multiple email domains like domain2.com, domain3.com, and domain4.com.

Is there anything preventing me from doing a cutover on those MX/SPF records first before I cutover our main domain domain1.com (which is also our internal domain name, I didn't set it up!)? All domains are set up as federated.

This would be great for me because I can bring our smaller companies onto office 365 first, reconfigure their blackberries, iphones, and outlook, and then move over our main company. Will this effect our daily sync that goes on from O365 to my on premises server?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Briantist posted:

I don't know enough about the O365 process to say whether it would affect its intricacies (especially the daily sync and all that), but in general you shouldn't have a problem cutting over one of the domains, as long as the 365 side is ready to receive e-mails from the outside world. I've done that type of cutover moving between many different types of mail systems, but never exchange to hosted exchange (and never a system where the two were "aware" of each other like this).

They're not really aware of each other besides O365 pulls nonsynced email from our onsite Exchange 2010 server, as far as I know, this isn't bidirectional.

O365 is ready to receive emails for these accounts, I licensed them up and they have some downtime next week so I'm going to do it for them and see how it goes (only 2 users). They both have blackberries which will need to be wiped and then reactivated, which is probably going to be a bigger pain in the rear end than doing the actual cutover, but hey, here we go.

I set the TTL for their MX records to an hour so when the cutover happens it should be pretty quick.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Does anyone here have a link to the proper way to create new users once you cutover to O365?

I've been reading even more about the cutover process and once I get everything over to O365 w/SSO and DirSync, you have to convert your users to Mail Enabled Users (otherwise, once you decommission onpremesis exchange, you run into problems). From what I can tell, the only way to do this is to use the attribute editor in AD or I believe you can also use powershell? It's not the biggest of deals but it would be nice if there was a way to create a "New -> MEU" right out of the GUI.

Is this possible?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
It's really loving aggravating how Microsoft is treating Public Folders WRT O365.

Should I just create a new shared Mailbox called Public Folders? Or do I need to create a new Room Mailbox for each room calendar?

And that means everyone will have to manually add it to their outlook since I don't want to grant full access. Or can I grant full access and then granularly control permissions through outlook?

Please don't say sharepoint :ohdear:

Thanks Microsoft.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Hey, Room Mailboxes are neat. 85% of my public folders are now gone. Apologies for the hissy fits I throw in here, I have no one to bounce ideas off of since I'm a 1 man shop.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Yeah man! Room/Shared Mailboxes are basically the proverbial poo poo.

Getting people to use them is the hard part, I've found.

Well, I'm throwing them into the fire next week when I delete the AllConferenceRoom shared calendar!

Now I have no loving idea how to deal with my 3 shared contacts Public Folders.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Will Styles posted:

Anyone else get screwed by the iOS update recently?

For those who don't know some users who update their iOS on mobile devices may begin to cause a high amount of transaction logging. Unfortunately I don't work at a place where I have any control over what my users do with their devices so I have to deal with it as it comes up. The solution seems to be to have them recreate their ActiveSync profile on the device after they update. At least I only have 10,000+ iOS devices in my environment :suicide:

Yep, that was fun!

I just made some screenshots from my iphone and pasted them into an email with quick directions. Thank god they pushed 6.1.1 out to the 4/4S quickly (I guess the 5 wasn't affected?)

slartibartfast posted:

Anybody have a basic introduction to Room Mailboxes that I can share with my managers?

Mine was essentially "Book a meeting in outlook, select the room, here's the room list, deal with it, the shared calender is read only, sorry, kthxbai!" and I threw a few tutorial links out there.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
So after a bunch of back and forth, my boss decided O365 wasn't going to work and we're going to implement a 2 server DAG for our E2010 setup. The problem is, the email server is 2008 R2 Standard and we need it to be enterprise. How hosed am I?

I guess we'll have to install the server in the DR facility, migrate the email to it, point everyone at it, and then rebuild the server her with R2 Ent and add it to the DAG? Or has anyone here done an in place upgrade of Windows with Exchange installed?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Thanks, that's what I thought. I had found a bunch of people saying you can do it but it's unsupported, so yeah, it's not the best idea to do it on such an important server.

Thanks!

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Briantist posted:

LmaoTheKid, what were the problems you had migrating to o365? Were they more related to your environment or the process in general?

A little bit of both, combined with how hosed up the documentation is for implementing things. It just got really loving annoying plodding through tons of links to find outdated information and BPAs WRT Azure and Active Directory and creating new accounts and blah blah blah.

It honestly just seems easier to go with expanding our in house server to a DAG with our DR facility.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Make sure the Macs have the latest versions of the office for mac Service Packs installed.

also gently caress Office for Mac in an enterprise environment to hell.

Yep. The new mail.app plays perfectly well with Exchange, just use that.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Can anyone point me to how ActiveSync handles multiple Exchange servers?

I'm going to be migrating our Ex2010 to another Ex2010 (different server name) box in our offsite hosting. Both will have all roles installed. If I point incoming mail to the new box and then slowly migrate mailboxes over to the new one, create the proper send connectors, how would activesync handle the mailboxes moved to the new box if they're pointed towards the old server? Would I need to point the devices to the new server?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

HTTPS => Your Outside Firewall => Your Exchange 2010 Client Access server

After that client access requests will find whatever mailbox server your user lives on. All by itself!

Your devices should all be using the same Client Access Server address. For 99% of my clients this is mail.company.com.

Holy gently caress thats awesome. That makes things so much easier, as I'll probably move our mobile.company.com address over to the DR site and then slowly move my mailboxes over. Now I just need to figure out where I need to point my Blackberry Piece of crap server (I assume to the new one) and I can move at my leisure.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
I'm at the point with my mimecast transition where they're pushing me pretty hard to enable journaling. I'm in the process of eventually moving all of our email to our DR facility where there's a much beefier server and more disk space.

I'm right in thinking journaling on the old machine at this point is a no go, right?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

wyoak posted:

Not directly Exchange, but it's related, so - we're looking at getting off of Postini (now Google Apps), since it seems to be like 2x the cost of most similiar SaaS offerings...does anyone have opinions of companies like EdgeWave, PostLayer, MX Guardian, or similar?

Get a quote from mimecast. They're pretty great and I haven't set up anything aside from their spam filtering yet.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
If I'm moving my mailboxes to a new server with a different name, do both servers need to be on the same rollup level? Or can I go with the newest one on the new server? I think I'm on 4 on the current one.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

You should be OK, although I try to keep all my Exchange servers at the same rollup/SP level just to avoid any potential problems. Last thing I want to do is have a horrible bug occur because of version mismatches in some stupid MAPI subsystem or something.

Yeah, that's true, and the new server is in Philly so it would be a bit of a pain to have to get down there if something locks up during the move (though Accela Express gets me there in 40 mins from NYC so its not that big of a deal)

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Pretty funny you should mention that, my firm is based outside of Philly.

We're some big rear end datacenter near the Drexler campus right up the street from the train station. It's super easy for me to get to. Still, I'd rather not make that trip if I don't to have to.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
So, I have my second Exchange 2010 server installed. Different host name, in my DR site.

I've read that I don't need send connectors because E2010 is site based so they should pass email back and forth.

So now I'm just a bit overwhelmed as to wha tI need to do. I guess my first order of buisiness should be to get a new cert with SAN of the new machine name, the Activesync/webmail address, AND the old host name? And I can run that alongside the current one, correct?

If anyone has a link to a good guide, i'd GREATLY appreciate it, and any help/pointers/caveats to look out for.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Syano posted:

What is your end goal in this scenario?

To slowly begin to migrate our mailboxes over to the new machine and decomission the old one.


The problem I can't seem to wrap my head around is how I maintain the two servers at the same time and keep activesync/OWA going.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
If I add the hostname of my second server to the SAN on my certificate, do I have to do anything like revoke and reissue the new cert?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

I didn't think that was possible without invalidating the original certificate in the first place.

I usually get my new shiny certificate, and then remove/re-add it on all Exchange servers before proceeding further.

Weird, the support guy at the cert authority who i talked to this morning said I shouldn't have to replace the cert.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
So, after months from putting down the migration from one 2010 box in our home office to another 2010 box in our DR site, I'm getting back into it and I just realized I never set up a CAS array. Good job, me.

How hosed am I creating this after the fact? I have about 50 users, so its really not the biggest of deals to go around and point them at the new CAS array.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

What do they point at now? Just create a new array, with something like mail2.yourcompany.com, test it, and if it works, change the main DNS record for mail.yourcompany.com or whatever it is pointing at to look at the new CAS, if that makes sense.

Right now the CAS is just the server name. I for some stupid reason didn't create a CAS for a single server when I did the initial install/migration from 2003.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Yeah CAS should be the outside address name (mail.yourcompany.com) and should be set up with Split DNS, at least for Exchange 2007+.

Odd, everything I'm seeing says that the CAS array shouldn't be advertised outside of the network.

Anyway, I'm way behind on Exchange updates anyway so my first order of business is to get both servers on SP3 and the latest rollup before doing anything.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Whatever the virtual IP is of the CAS array, you want stuff on the outside to resolve to that.

So right now, for example, you might have something like mail.poopyfarts.org, on your firewall that gets translated to your CAS internal IP address (192.168.5.1) which is cas01.poopyfarts.local, but should also be set up in your internal DNS to point mail.poopyfarts.org => 192.168.5.1 internally.

Instead, you'll have mail.poopyfarts.org point to the virtual IP of your CAS array from the outside (so the firewall goes to that instead of 192.168.5.1) and likewise for the internal DNS.

Thanks, I'll start trying to get this in order.

So for about 50 mailboxes/300 gigs or so of email on 2010 SP1, about how long can I expect for downtime? My boss is traveling in Japan right now and getting kind of bitchy about this downtime but the next few months are pretty much booked solid so it would be good to have an estimate. Obviously CPU and other things factor into this, but can anyone give me an estimate, I'm seeing 30 mins to 2 hours on various sites but I have no idea what their install conditions are.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

If your current CAS is on its own machine, no downtime, really. If you have one box with all the roles, that is a bit more complicated. Really you should be able to do all the testing with the mail2.company.com DNS record before switching over.

Yeah, we're all in one. I'm probably just going to go in for an hour or two on friday when everyone is off. Thanks for all your help!

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Just checking, Junk Email for outlook is processed client side right? We use Mimecast and I'm trying to figure out how to shut that poo poo off since we don't need double filtering. I'm trying to figure out if it's a server setting or a GPO thing I have to deploy.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Anyone have a good cross site redirection tutorial? I'm finding a few but they leave a lot to be desired.

My last step here is getting that working so I can start moving mailboxes without disrupting OWA/ActiveSync.

The new server is not external facing yet, just accessible via VPN in all offices and until we're ready to cut over to it as the new server, I'd kind of like to keep it that way.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
Holy loving gently caress. I got everything working.

Servers have a new re-keyed cert with both internal and the external host names on it. OWA and ActiveSync Proxying works. Email flows back and forth through both servers and externally. Goddamn, can I really start moving mailboxes in a week or so?

When you guys say I have to "touch" all the clients afte rI move their mailboxes, what exactly do you mean by that? And does the offline cache need to rebuild or will I be ok there?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

Gyshall posted:

Really depends on how they are set up now. I'd pick a guinnea pig user and see how they react to being moved (after telling them of course.)

Ideally you should have all clients Outlook profile pointing at mail.whatever.com as the Client access server (new or old) which then will update automatically.

I think the 2003 => 2010 documentation says to create a legacy.whatever.com address and then you set up reverse proxying for mail.whatever.com to legacy.whatever.com. That should handle all client access nonsense.

I can use myself as a guinea pig, I don't care.

Unfortunately the way I originally set up was for everyone to point to hostname.domain.com and never created a 1 server CAS array (which I asked about earlier). According to various articles I've seen, if I had set up a 1 server CAS array all I'd have to do is add the new server to the array and when I do the mailbox move it just automatically flips over (which I guess is what you said).

Since I have split DNS I should probably set up a CAS array for our external domain internally and then point everyone to that, and then add the new server to the array?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
So, uh, WTF did I miss here? I moved my London office over to our new email server and outlook just picked up the change automatically. Is this the fabled improvements made to RPC or something in one of the Service Packs?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

NevergirlsOFFICIAL posted:

that's normal and that's why you keep the old exchange server up for a while after the migration - outlook clients that hit the old server will be informed of the new one.

So odd. Everything I read said that unless you were using a CAS (even with one host) that you'd have to go and touch every client individually. I'm certainly not complaining! This was 2010 to 2010.


Gyshall posted:

you're doing it right

:3: Thanks!

One more question, how does it work with Blackberry? Should I wait to migrate my remaining BB users and then point the BES server at the new email server? Or will it proxy the request to the other server?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

NevergirlsOFFICIAL posted:

Move all your BES users (and besadmin account) at once and then point BES to new server. As long as you're on 2010 shouldn't have to do anything else. it took us a long time with RIM support to get BES working after migration to 2013 because 2013 doesn't do MAPI. The resolution was reinstalling a bunch of poo poo in a specific order (of course) that wasn't documented very well anywhere (of course).

Ok, since they're spread over different offices, I'll leave them for last.

NevergirlsOFFICIAL posted:

only if the old exchange server is no longer accessible. so you will have to do that for users who are on vacation or have their computers off.

Great, I don't plan on shutting that serve roff for another month and I'll have everyone moved over by then. Thanks!

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

NevergirlsOFFICIAL posted:

don't forget public folders

Already replicating. And OAB has been moved too.

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)
So, mailboxes are finally all moved, OAB is rehomes, Public folders are replicated. Today I'm rehoming mailflow to the new server and changing DNS to point to th enew external IP for Activesync/webmail.

Is there anything else I need to do to fully transfer everything over to the new 2010 server from my old 2010 server?

Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

The Electronaut posted:

New public folder set as the default on your mail DB(s)? Special mailboxes migrated? Not sure of your architecture so those are two that jump off my head at first glance. I assume you have a CAS array and your Outlook users are using a VIP for connectivity instead of a single CAS.

When time to remove the old server, I'd do a pull the plug/power down cool off, followed by gracefully uninstalling it.

All clients are cut over to the new server. Public folders are happily replicated. Special mailboxes are moved. SMTP send and recieve are rehomed. Firewall is set. Public and private DNS are changed to the new proper internal and external IPs.

I can't really think of anything else. I'll shut it down on Monday and see how it goes.

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Matt Zerella
Oct 7, 2002

Norris'es are back baby. It's good again. Awoouu (fox Howl)

The Electronaut posted:

Nice. Any internal mailing server systems that may have connected via IP or machine name for SMTP/POP3/IMAP? Got your backups configured? Monitoring? Scripts?

Waiting on a vendor to flip something over for mail. I have a "local relay" recieve connector that I allow basic authentication based on IP

Backups are running nightly.

Monitoring is off right now as I'm in the process of redoing it.

I do t run any scripts so no worries there.

Feeling pretty good. Ill power it down I. Monday to see if we have any issues.

Good god I'm almost do e with this nightmare.

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