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devmd01
Mar 7, 2006

Elektronik
Supersonik
I somehow pulled off a complete exchange 2013 migration to a new data center yesterday, in the middle of the day, with zero downtime or impact to users. 2013 is so much easier and robust to do a move it's not even funny.

Added new mailbox servers to the dag and got the DBs replicated, then after that it was just a matter of disabling a cas server in the NLB, migrating it to the new location, updating internal/external DNS, then migrating the second CAS once traffic had drained from the old location.

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SeaborneClink
Aug 27, 2010

MAWP... MAWP!
Exchange 2013+ owns. Death to 2010. 2007 is the stone age.

Thanks Ants
May 21, 2004

#essereFerrari


Exchange usually gets SAN certs over wildcard ones because internal and external DNS is likely to be different. Even if your internal DNS is just a subdomain of your external name, a wildcard only covers *.domain.com and not *.corp.domain.com.

milk milk lemonade
Jul 29, 2016
Got it. Thanks! I don't really know anything about SSL certs and I learned something today.

dexter6
Sep 22, 2003
OK semi-follow-up question...

I don't have an archive button in outlook 2016 for mac. I've googled and seems like others have this issue, but couldn't find a resolution.

Anyone know why?

wa27
Jan 15, 2007

I figured out our copier issue. We had a box acting as an SMTP relay (used for spam filtering). Disabling that let it connect to 365.

Beefstorm
Jul 20, 2010

"It's not the size of the tower. It's the motion of the airwaves."
Lipstick Apathy

wa27 posted:

I figured out our copier issue. We had a box acting as an SMTP relay (used for spam filtering). Disabling that let it connect to 365.

Better than my solution.

I had a Konika Minolta that refused to scan to email through 365. I worked with Microsoft and Konika on the phone at the same time. They both eventually agreed that the printer is simply not compatible with Office 365, and that I had to come up with a different solution.

I ended up putting an SMTP relay on one of the Windows VMs, and had it send to that. Then that would send to Office 365. It worked...just stupidly.

Dyscrasia
Jun 23, 2003
Give Me Hamms Premium Draft or Give Me DEATH!!!!

devmd01 posted:

I somehow pulled off a complete exchange 2013 migration to a new data center yesterday, in the middle of the day, with zero downtime or impact to users. 2013 is so much easier and robust to do a move it's not even funny.

Added new mailbox servers to the dag and got the DBs replicated, then after that it was just a matter of disabling a cas server in the NLB, migrating it to the new location, updating internal/external DNS, then migrating the second CAS once traffic had drained from the old location.

I thought that NLB was unsupported at this point? We had all sorts of issues until we added F5 LTMs. The Exchange 2016 environment I'm building will use the Netscalers we already use for Citrix.

Not to take away that the client connectivity of 2013 and 2016 blows away 2010.

devmd01
Mar 7, 2006

Elektronik
Supersonik
Barracuda NLB appliances. The generic term. And yeah, the Microsoft NLB causes more trouble than it's worth, especially in a VMware environment.

Dyscrasia
Jun 23, 2003
Give Me Hamms Premium Draft or Give Me DEATH!!!!

devmd01 posted:

Barracuda NLB appliances. The generic term. And yeah, the Microsoft NLB causes more trouble than it's worth, especially in a VMware environment.

Gotcha, I assumed the MS one. If I remember right, DNS round robin is the way to go without a load balancer.

Snorri
Apr 23, 2002
So I installed a new Exchange 2016 VM for my office users this year and everything has been peachy minus one issue: IPv6 rejections from Google hosted mail servers. I would say this only happens around 10% of the time, but it is insanely annoying. We are on Comcast Business internet and cannot receive static IPv6 addressing yet (and we are fortunately dumping Comcast by the EOY anyway). So on my Postfix server I disabled IPv6 completely and everything was fine as I could setup SPF/RDNS with IPv4. Everything I have read about disabling IPv6 with Exchange 2013/2016 says it will kill the whole shebang. I can quasi-confirm that as I tested something about a month ago and the VM stopped booting completely, whoops. After re-enabling IPv6 it was a happy camper again. The kickbacks from Google use the IPv6 address of the 6TO4 adapter in my VM, not the IPv6 of the firewall the mail is going through, so that is even more irritating because at least I could band-aid it otherwise.

Anyone have any thoughts on this?

Dans Macabre
Apr 24, 2004


My goal: to move all mailboxes to Exchange Online and have the users turn on the computer the next day and update automatically.

Is there any "Microsoft Way" to do profile migrations when moving from on-prem to o365? I know skykick and bittitan have tools. In the past I have used bittitan and I've also forced new profile creation via GPO.

I'm also trying to think if there's any reason to NOT create a new profile? The only thing I can think of is signature transfer, and we do our signatures centrally so that's not needed.

anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum

NevergirlsOFFICIAL posted:

My goal: to move all mailboxes to Exchange Online and have the users turn on the computer the next day and update automatically.

Is there any "Microsoft Way" to do profile migrations when moving from on-prem to o365? I know skykick and bittitan have tools. In the past I have used bittitan and I've also forced new profile creation via GPO.

I'm also trying to think if there's any reason to NOT create a new profile? The only thing I can think of is signature transfer, and we do our signatures centrally so that's not needed.
You could delete their old mail profile and force Outlook to run the new mail wizard at next logon

Thanks Ants
May 21, 2004

#essereFerrari


If you're migrating from Exchange then it's quite hard to not have everything Just Work[TM]. Unless you're going from pre-2013 Exchange, gently caress that.

SeaborneClink
Aug 27, 2010

MAWP... MAWP!
What Thanks Ants said, also set the proper Outlook first run GPO's.

wa27
Jan 15, 2007

Context: We switched from Outlook 2010/Exchange 03 to O365/Office2016 this week.

In my outlook, I can look at "Suggested Contacts" and it has apparently every email I've ever sent/received from. A few hundred addresses. When I look at my boss's outlook, she has no suggested contacts, despite having 5 times the email history I have.

Is there anything I can do to force those suggested contacts to be created? I am needing to rebuild her autocomplete list (no I didn't save the nk2 file or whatever the Outlook 2010 equivalent is, and that was dumb). It's easy to add back in all staff from the GAL, but I'm trying to get everyone she's ever sent to as well. I figured the suggested contacts is probably the easiest way.

anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum

wa27 posted:

Context: We switched from Outlook 2010/Exchange 03 to O365/Office2016 this week.

In my outlook, I can look at "Suggested Contacts" and it has apparently every email I've ever sent/received from. A few hundred addresses. When I look at my boss's outlook, she has no suggested contacts, despite having 5 times the email history I have.

Is there anything I can do to force those suggested contacts to be created? I am needing to rebuild her autocomplete list (no I didn't save the nk2 file or whatever the Outlook 2010 equivalent is, and that was dumb). It's easy to add back in all staff from the GAL, but I'm trying to get everyone she's ever sent to as well. I figured the suggested contacts is probably the easiest way.
What's the indexing status?

wa27
Jan 15, 2007

anthonypants posted:

What's the indexing status?

It says it's completed.

Edit: I found an autocomplete Dat file that includes everyone I need. Now to just figure out how to import it into 2016.

wa27 fucked around with this message at 18:12 on Nov 16, 2016

Dans Macabre
Apr 24, 2004


Thanks Ants posted:

If you're migrating from Exchange then it's quite hard to not have everything Just Work[TM]. Unless you're going from pre-2013 Exchange, gently caress that.

I'm going from 2010.

Thanks Ants
May 21, 2004

#essereFerrari


Then you're in luck and it's gotten easier since I last touched it:

https://blogs.technet.microsoft.com/exchange/2016/02/17/office-365-hybrid-configuration-wizard-for-exchange-2010/

I'd still take them up on the offer of a Hybrid License if you have the capacity to run up another server.

Dans Macabre
Apr 24, 2004


Thanks Ants posted:

Then you're in luck and it's gotten easier since I last touched it:

https://blogs.technet.microsoft.com/exchange/2016/02/17/office-365-hybrid-configuration-wizard-for-exchange-2010/

I'd still take them up on the offer of a Hybrid License if you have the capacity to run up another server.

Yep I did this last night and went pretty smoothly.

When I move people's mailboxes over I'm going to try flipping the workstations with deploymentpro. Last time I tried it I had 25% success rate.

Dans Macabre
Apr 24, 2004


Can I just say how amazed I am that this whole thing literally Just Worked. I remembered exch2010 to hybrid being a pain in the rear end last time I did it. This was a breeze. RIP anything that competes with Office 365 (including my company lol)

devmd01
Mar 7, 2006

Elektronik
Supersonik
God I wish the German parent company didn't have a cloud ban, it's holding back what we can do do for the business in a big way. I have a perfect use case for O365 (lots of sister companies) but we can't.

Not to mention adding those skills to my resume.

devmd01
Mar 7, 2006

Elektronik
Supersonik
So apparently if a 2013 mailbox server that is the active DAG member runs out of memory it fubars your entire environment, something to add to the monitoring list!

anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum
If I wanted a query-based/dynamic distribution group, I'd need either an Exchange server or an Azure premium license, right?

Dans Macabre
Apr 24, 2004


Hey you guys! Moved an org to hybrid, all user mailboxes are on Exchange Online.

We have a signature management software on the on-prem server that needs to stamp every outgoing message. This is working great when sending to external addresses, but internal messages (365 to 365) are not stamped.

Is there a way, and is it advisable, to have messages go from Exchange Online mailbox, to the on-prem server to be stamped, and then back to Exchange Online mailbox? How do I achieve this?

anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum

NevergirlsOFFICIAL posted:

Hey you guys! Moved an org to hybrid, all user mailboxes are on Exchange Online.

We have a signature management software on the on-prem server that needs to stamp every outgoing message. This is working great when sending to external addresses, but internal messages (365 to 365) are not stamped.

Is there a way, and is it advisable, to have messages go from Exchange Online mailbox, to the on-prem server to be stamped, and then back to Exchange Online mailbox? How do I achieve this?
In Exchange Online, set up an outbound connector that sends mail to external contracts through the on-prem server. You don't need to send it back to Exchange Online if you're in a hybrid environment.

Dans Macabre
Apr 24, 2004


anthonypants posted:

In Exchange Online, set up an outbound connector that sends mail to external contracts through the on-prem server. You don't need to send it back to Exchange Online if you're in a hybrid environment.

No I want INTERNAL email (o365 to o365) stamped with signature.

anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum

NevergirlsOFFICIAL posted:

No I want INTERNAL email (o365 to o365) stamped with signature.
Okay, set up an outbound connector in Exchange Online that routes all mail to internal domains through the on-prem server, then. Since it's a hybrid environment, your on-prem Exchange server will still make sure the mailbox is synced to Exchange Online, so you don't need to reroute the mail back out. When you set up the connector, you can tell it to use that connector on all of your internal domains, a list of domains you give it, or you can make a transport rule that has those domains in it (and/or any other criteria) that references the connector.

Dans Macabre
Apr 24, 2004


ok nice let me try that

Dans Macabre
Apr 24, 2004


Wait a minute, I already have that... as part of the hybrid config. That's exactly what the hybrid config wizard creates. What am I missing?

Thanks Ants
May 21, 2004

#essereFerrari


Are you sure it doesn't just route unknown mailboxes on the internal domain to your Exchange server?

Internet Explorer
Jun 1, 2005





Sounds to me like it's time to switch to a signature/disclaimer software that works with O365.

Dans Macabre
Apr 24, 2004


Thanks Ants posted:

Are you sure it doesn't just route unknown mailboxes on the internal domain to your Exchange server?

I mean, in practice I think that's what it's doing. But the connector setup you're describing, is what I have.


Internet Explorer posted:

Sounds to me like it's time to switch to a signature/disclaimer software that works with O365.

I looked at CodeTwo (which is what we're using on prem) and their solution involves routing through their own azure-managed server. I'm thinking that just adds another thing into the mix that I can't control easily. Am I thinking about this the wrong way? Is there a better solution?

The built in transport rules in o365 aren't sophisticated enough for what we need I think.

Dans Macabre
Apr 24, 2004


OK I have my hybrid deployment Office 365 + Exch 2010. I also have a new Exch 2016 server. I want to remove the Exch 2010 server.

What do I need to do to set up hybrid to 2016? Can I just re-run the hybrid configuration wizard on the new server to create all the connectors?

incoherent
Apr 24, 2004

01010100011010000111001
00110100101101100011011
000110010101110010
I would suspect you migrate all roles to 2016 (what's left of them, anyway), then run the configuration wizard.

SeaborneClink
Aug 27, 2010

MAWP... MAWP!
3 days ago we started receiving sporadic NDR's

code:
Remote Server returned '< #5.4.318 smtp;550 5.4.318 Message expired, connection reset (SuspiciousRemoteServerError)>'
code:
Generating server: BN3PR1101MB1185.namprd11.prod.outlook.com
Receiving server: BN3PR1101MB1185.namprd11.prod.outlook.com
Total retry attempts: 277

12/8/2016 10:39:48 PM - Server at BN3PR1101MB1185.namprd11.prod.outlook.com returned '550 5.4.318 Message expired, connection reset (SuspiciousRemoteServerError)(450 4.4.318 Connection was closed abruptly (SuspiciousRemoteServerError))'
12/8/2016 10:28:59 PM - Server at outlook.contoso.com (xx.xx.xxx.xxx) returned '450 4.4.318 Connection was closed abruptly (SuspiciousRemoteServerError)'
Further investigation showed that there were 170 messages held in EOP in 'Pending' status from a decent cross section of users, all of whom were otherwise unaffected and were able to both send and receive mail without issue.

Connectivity analyzer indicated no other issues mailflow wise across the mailboxes I tested, all of whom had mail that was held. SPF checks passed without issue and obviously the Exchange server was online and receiving mail.

I double checked the valid receive connectors and updated the Microsoft provided blocks, some of the ip ranges were mis-configured (a couple /22 moved to /23, a /25 went to /24, etc) however this did nothing to resolve the queued mail.

About this time I was told that we had another separate production environment that was also experiencing a similar issue.

I ended up logging into the primary ASA (5505) and ended up setting
code:
no inspect esmtp
in the policy-map inspection_default, reload and the queue started to magically clear.

Executing this change resolved the issue in both environments, but there was just no method to the madness as to why this just suddenly decided to break or why only two of 8 envs (with EOP, on-prem exchange & an ASA) were affected, other than some gradual Microsoft related change in EOP.

Maneki Neko
Oct 27, 2000

SeaborneClink posted:

I ended up logging into the primary ASA (5505) and ended up setting
code:
no inspect esmtp
in the policy-map inspection_default, reload and the queue started to magically clear.

Executing this change resolved the issue in both environments, but there was just no method to the madness as to why this just suddenly decided to break or why only two of 8 envs (with EOP, on-prem exchange & an ASA) were affected, other than some gradual Microsoft related change in EOP.

I feel like ASA/PIX inspects/fixups loving things up has been a constant for the last 15 years I've been working in IT.

Maneki Neko fucked around with this message at 04:37 on Dec 11, 2016

MrMojok
Jan 28, 2011

I have a sort of an odd question. I don't technically work at an MSP, but we might as well be one with the way things have gone for the last couple of years.

One of our client companies is changing their name. What they want, is that when the change goes into effect, which is soon, they want anyone who emails them at username@oldcompanyname.com to receive an auto-reply saying "We have changed our name! In future, please email me at username@NEWcompanyname.com rather than username@oldcompanyname.com. Thank you!"

I guess their thinking is, if enough of their contacts and consultants receive this often enough, it will annoy them to the point where they'll actually change their address books and email the new company email addresses. They are pretty firm on their desire for this, and the way things work here, if $ClientCompany wants something, they get it.

Currently each user's exchange account has username@oldcompany.com set as their primary/reply address, and then username@NEWcompanyaddress is in alias. On the day this change goes into effect, which is unfortunately very soon, I will switch the primary/reply to the @NEWcompanyname.com and keep the @oldcompanyname.com as an alias.

My first idea, since they only have about 15 employees, was to go at this from the client end. I created an email alias for my own account, went into OWA and looked at inbox rules. I could say IF email sent to address username@oldcompanyname.com, THEN do something. But the OWA options for what I could do were limited: move the msg to a folder, mark it with a category, delete it.

Next, I started experimenting in Outlook. In Outlook 2010 I found in rules and alerts that there was a way to do exactly what I wanted. However, after some experimentation, I realized that the auto-respond message was being sent back regardless of whether the sender had emailed mrmojok@oldcompanyname.com or mrmojok@NEWcompanyname.com. In other words, I couldn't see how to make it reply only if the sender sent to mrmojok@oldcompanyname.com. So that won't work.

So now I am wondering if there is a way to do this from the server side, which is probably how I should have approached this in the first place. We are using Exchange 2010, update rollup 15. Does anyone know a way I might be able to have exchange, only when it receives an email to someone@oldcompanyname.com, to reply with an automated message?

I hope this makes sense.

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anthonypants
May 6, 2007

by Nyc_Tattoo
Dinosaur Gum

MrMojok posted:

I have a sort of an odd question. I don't technically work at an MSP, but we might as well be one with the way things have gone for the last couple of years.

One of our client companies is changing their name. What they want, is that when the change goes into effect, which is soon, they want anyone who emails them at username@oldcompanyname.com to receive an auto-reply saying "We have changed our name! In future, please email me at username@NEWcompanyname.com rather than username@oldcompanyname.com. Thank you!"

I guess their thinking is, if enough of their contacts and consultants receive this often enough, it will annoy them to the point where they'll actually change their address books and email the new company email addresses. They are pretty firm on their desire for this, and the way things work here, if $ClientCompany wants something, they get it.

Currently each user's exchange account has username@oldcompany.com set as their primary/reply address, and then username@NEWcompanyaddress is in alias. On the day this change goes into effect, which is unfortunately very soon, I will switch the primary/reply to the @NEWcompanyname.com and keep the @oldcompanyname.com as an alias.

My first idea, since they only have about 15 employees, was to go at this from the client end. I created an email alias for my own account, went into OWA and looked at inbox rules. I could say IF email sent to address username@oldcompanyname.com, THEN do something. But the OWA options for what I could do were limited: move the msg to a folder, mark it with a category, delete it.

Next, I started experimenting in Outlook. In Outlook 2010 I found in rules and alerts that there was a way to do exactly what I wanted. However, after some experimentation, I realized that the auto-respond message was being sent back regardless of whether the sender had emailed mrmojok@oldcompanyname.com or mrmojok@NEWcompanyname.com. In other words, I couldn't see how to make it reply only if the sender sent to mrmojok@oldcompanyname.com. So that won't work.

So now I am wondering if there is a way to do this from the server side, which is probably how I should have approached this in the first place. We are using Exchange 2010, update rollup 15. Does anyone know a way I might be able to have exchange, only when it receives an email to someone@oldcompanyname.com, to reply with an automated message?

I hope this makes sense.
It's going to be much harder if user@oldcompany is an alias for user@newcompany, because Exchange is going to treat them like the same thing. Someone else might have a better solution, but the only thing I can think of is an oldcompany Exchange server with a transport rule to send the autoreply to the sender and then forward the email to the newcompany Exchange server.

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