My work wants us to spin up Microsoft Exchange in the near future.

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Trx3141@reddit

Exchange 2019 EOL is Oct 2025. MS says: " We have moved the release date for the next version of Exchange Server to the second half of 2025. The next version will require Server and CAL licenses and will be accessible only to customers with Software Assurance " in [https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-server-roadmap-update/ba-p/3421389](https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-server-roadmap-update/ba-p/3421389)  Not 100% sure, but this might mean that you can't purchase new exchange unless you owned 2019. You would get the new version only through Software assurance. Which might mean - No Exchange OnPrem for new purchases. Am I interpreting this correct ?

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ottdriverssuck@reddit

You’ll need an active SA agreement for the next version. We already have one at my org so I’m not worried.

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hunterkll@reddit

Next version is going to align pricing with O365 for subscription pricing, like the current sharepoint is. So SA or not, you're in for a price adjustment.

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ottdriverssuck@reddit

Do you have a source for this information? Our SA agreement is paid until 2026 and my Microsoft rep has confirmed we will have upgrade rights.

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p38fln@reddit

That's the point of SA, consistent pricing. When you renew in 2026 you're going to be unpleasantly surprised.

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ottdriverssuck@reddit

Well considering you can't provide a source for your information, I take what you say with a grain of salt.

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p38fln@reddit

You aren't expecting a price increase or change to terms? They change licensing requirements all the time. SQL 2005 to 2008 they added a requirement to pay for a license for reporting servers, previously they were included in the license for a production server. A few years ago they changed the data center license from per CPU to per core. I can't say what they'll do but their past behavior has been to change licensing terms with the release of a new product, push out massive audits shortly after changing terms (you agree to audits if you're part of the VL program) and then charge the customer double for the appropriate licenses.

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hunterkll@reddit

thread here talking about it and some details about vNext [https://www.reddit.com/r/sysadmin/comments/10lvb9e/microsoft\_announced\_new\_plans\_for\_exchange\_server/](https://www.reddit.com/r/sysadmin/comments/10lvb9e/microsoft_announced_new_plans_for_exchange_server/)  pertinent part:  " The next version will require Server and CAL licenses and will be accessible only to customers with Software Assurance, similar to the SharePoint Server and Project Server Subscription Editions. We will provide more details on naming, features, requirements, and pricing in the first half of 2024. "

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ottdriverssuck@reddit

I've read this before, still no mention of any crazy price increase so I will wait for the details to be released. Regardless, I have 3 years to make a decision.

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xXNorthXx@reddit

Exchange on-prem isn’t going away. I can’t get into details but MS knows of a number of larger orgs that aren’t going to o365. Exchange Online works for a lot of use cases but not everyone can move either due to security requirements or scale… I know a few fortune 100 that will be running exchange on-prem or hybrid for years to come multi-PB developments that Exchange Online ingestion speeds are not viable.

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qlz19@reddit

Yeah, but how is that relevant to the idea: no new on prem Exchange servers? They are not talking about staying on prem, they are talking about deploying a brand new on prem Exchange server.

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hunterkll@reddit

You just buy 2019 and install it. Nothing crazy about it.

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qlz19@reddit

How many years does Exchange 2019 have left of support?

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hunterkll@reddit

2025, and vNext is slated to be released that year as a slot in easy in-place upgrade.

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xXNorthXx@reddit

If upper management wants in on-prem and they want to pay for a proper hardware for it, I don’t see any issue. It trains all the users on Exchange and makes transitioning to Exchange Online down the road easier if the business changes their mind. The only thing I’d stay clear from is ever deploying public folders.

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hunterkll@reddit

>Not 100% sure, but this might mean that you can't purchase new exchange unless you owned 2019. You would get the new version only through Software assurance. You can still buy 2019, that hasn't gone away. It's VL only though, no "Retail" SKUs.

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adx931@reddit

Brush up on your powershell. As nice as the web-based control panel is, you will ultimately need to run some powershell from time to time. For example, sometimes various components will not function after reboot, even if their specific services are running. Get-ServerComponentState and Set-ServerComponentState are your friends. Normally -Requester HealthAPI will do the trick, but if the failure happens after a botched update, try rotating through all the requester types if it's not obvious. Starting with 2013, they killed off most of the legacy horror show, and it was completely gone by 2016. I don't have any direct experience with 2019, but I understand it's 2016 with improvements.

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No-Style-5153@reddit

Mine is more for Office 365, but there's some solid stuff in it I wrote a long time ago. I've put it up on Github for anyone who needs it. [https://github.com/Scine/office365](https://github.com/Scine/office365)

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Hotshot55@reddit

> As nice as the web-based control panel I don't think I ever referred to any Exchange related GUI as "nice".

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ex800@reddit

>I don't think I ever referred to any Exchange related GUI as "nice". Depends what the comparison is to, I'll start with Groupwise...

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adx931@reddit

Groupwise was the only system that made me think, "Man, I really miss Domino"

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ex800@reddit

it was a long time ago, but the pain is burnt in...

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Velinnaria@reddit

... I had almost forgot that nightmare ever existed.

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bobsmagicbeans@reddit

compared to the horror of SCCM or SCOM, Exchange is super nice. that said, a good chunk of settings and info are missing from the GUI and only accessible via powershell

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Whatwhenwherehi@reddit

Yep. Forest and all are 16. Its 8.1 all over again.

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hunterkll@reddit

>Starting with 2013, they killed off most of the legacy horror show, and it was completely gone by 2016. I don't have any direct experience with 2019, but I understand it's 2016 with improvements. Yea, 2013 was the first version where the self healing really works well and doesn't require a shitload of handholding. Since then it's basically all been the same.  2019's nice that it can be installed on server core though instead of full GUI server.

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malikto44@reddit

If you have an air-gapped network, perhaps consider using Dovecot IMAP, RoundCube, or Zimbra? If you just want an appliance for this, buy a low-end Synology NAS, stuff two SSDs in it, go with RAID 1, and have HyperBackup back it up to a USB external drive, or even better, another NAS dedicated for backups. Going with a relatively simple SMTP/POP/IMAP server can be a lot easier, doesn't need the license fees, and can work just as well for a lot of tasks as going with full-blown Exchange.

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Dadarian@reddit

Do they have a good reason why they want Exchange? Who is asking for this and why? Like, I know it sounds silly but they’re important questions. If you’re not even sure why they’re making this decision, it’s a little weird that they would ask you to support it. Any company that wants to use on-premise Exchange should be able to make a good argument why they need it. There is a ton of risk when running the service yourself, and it’s important to understand the risk before jumping into it.

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hunterkll@reddit

>Any company that wants to use on-premise Exchange should be able to make a good argument why they need it. OP stated offline environment. Likely, they're using office and will want at least the some of the integrations provided by exchange. But, for what it's worth, Exchange will be the easiest to set up and manage out of a variety of options for most admins, and essentially runs/maintains itself. (At least since 2013, exchange before 2013 required a lot of hand holding....)

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EViLTeW@reddit

>But, for what it's worth, Exchange will be the easiest to set up and manage out of a variety of options for most admins, and essentially runs/maintains itself. (At least since 2013, exchange before 2013 required a lot of hand holding....) If GroupWise had a web interface that wasn't absolute dogshit, I would 100% recommend that over Exchange. It's waay better (on the server side) for on-prem environments... but the web client is, in fact, absolutely dogshit.

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hunterkll@reddit

Dear god why. That's like suggesting lotus notes. Just without note/domino's capabilities of integration and management.... half the point of exchange is what it integrates with !

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EViLTeW@reddit

OP wants an air gapped email platform. GroupWise (server side) is just better than Exchange. Single instance storage is incredibly efficient, especially in an air gapped environment. Their calendaring system is just plain better. Management of the system is significantly easier. It runs on Linux (10 points to slitherin). The problem with GroupWise, is its lack of a fully functional client that isn't a Windows fat client. The place I used GroupWise move to o365 more than 10 years ago, and I'd never go back to on-prem email if given the choice... But if GroupWise had a web UI as functional as the current owa and I *had* to go back on-prem, I would almost certainly recommend it over dealing with exchange on-prem again. Almost everyone who trash talks GW either never used it or used it 25 years ago as an end user.

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hunterkll@reddit

>Single instance storage is incredibly efficient, especially in an air gapped environment. > >Their calendaring system is just plain better. > >Management of the system is significantly easier. > >It runs on Linux (10 points to slitherin).  Storage wise, exchange is pretty lean. almost zero overhead over what's stored in the system.  Their calendaring system has ready made hooks that integrate with systems i'm already using? \*especially\* when sharepoint's in play.  Management of the system..... how much management do you think exchange has? Not much if you do it right, it's practically set it and forget it. Before 2013 this was wildly different, however.  Linux, windows server, AIX, solaris, HP-UX, OpenVMS - I don't really care what platform $thing runs on. Whatever's needed. Server OS is practically irrelevant.  >Almost everyone who trash talks GW either never used it or used it 25 years ago as an end user.  I've used and administrated it within the past 6 years. Still a hard pass from me. That was only because it was in play at a client site.  >The place I used GroupWise move to o365 more than 10 years ago, and I'd never go back to on-prem email if given the choice... But if GroupWise had a web UI as functional as the current owa and I *had* to go back on-prem, I would almost certainly recommend it over dealing with exchange on-prem again.  I'd be the opposite, because exchange literally runs itself. Almost zero admin time/overhead, set it and forget it (outside of installing CUs)

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Dadarian@reddit

Ah. I didn’t see offline environment part. Curse my ADHD. This is far outside of my field. I don’t know offline environments very well.

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catherder9000@reddit

> I don’t know offline environments very well. Think of everything you do in the cloud, but now do it 10 times faster (or more) because it's on your internal network. The downside is you now also have to administrate the server and applications that run on it so you can do xyz. For most of us the upsides outweigh the downsides.

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hunterkll@reddit

It's the same as online environments, except no internet! Stuff still works exactly the same.

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trippedonatater@reddit

Yes! Also: managed services are almost always cheaper than engineer time.

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1z1z2x2x3c3c4v4v@reddit

> There is a ton of risk when running the service yourself This is a megaton of risk. Almost guaranteed pain and failure in the future. Hosting your own Exchange server today, for inexperienced techs, is suicide.

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ZAFJB@reddit

> There is a ton of risk when running the service yourself, There is not really

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tonykrij@reddit

This. I'm so thankful for NOT having to support Exchange servers anymore. Don't go backwards in time. For your future jobs as well...

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RikiWardOG@reddit

Ya managing DB sizes and stuff F THAT. So glad I don't have to deal with on prem exchange

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hunterkll@reddit

Managing DB sizes? What version of exchange are we talking about here? Properly configured systems .... i've ... never had to manage DB sizes? If you mean mailbox quotas and assignments to DBs that's one thing, but directly ? Never.  Just make sure you have a proper backup system in place to prevent runaway logs and you're golden. Or use exchange NDP and circular logging and you don't even "need" that (though i still highly reccomend you have one...)  It's literally set it and forget it since 2013, even on complex setups....

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joefleisch@reddit

Managing DB size had to occur when the mailbox size is over provisioned compared to the DB disk size. Bad company policies are often involved along with little budget for proper sizing. I always did a 6-month maintenance of migrating mailboxes to new DB’s to clean up corrupt mailbox items. It was mobile devices and their calendar items creating bad items.

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occasional_cynic@reddit

Pre-Exchange 2010 SP-something the DB sizes were limited to 2TB as well unless you had a registry hack.

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ottdriverssuck@reddit

> There is a ton of risk when running the service yourself There's risk in O365 too, most people don't secure that properly either, which is why you see all these posts about $user's account being compromised haha.

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qlz19@reddit

Yeah, but do you somehow believe that a team who leaves themselves open in 365 is going to magically be secure on prem?

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ottdriverssuck@reddit

I never said nor implied that. Just noted an observation.

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qlz19@reddit

Yeah, but at least that team would have the extra bandwidth from not managing the infrastructure to maybe spend some time on security. It’s about removing workload to focus on other more important areas, like security.

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sidneydancoff@reddit

Keep in mind that unless you have an effective and audited maintenance program where your scanning for exchange vulnerabilities and routinely patching there should be a pause to review the risk.

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someguy7710@reddit

Eh, its not that hard. You should be fine.

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wallacehacks@reddit

It cracks me up how many self declared sysadmins are afraid to host anything themselves. Like I know 365 is easier but come on people this is literally what we are paid to do and why so many of us ask for big salaries.

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someguy7710@reddit

Right, you're just running shit on someone else's hardware. "Cloud" is nice, but it still needs to be managed. They've been promoting cloud for decades.

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rootbeerdan@reddit

What are you smoking, hosting exchange is a pain in the ass unless you don't care about uptime or deliverability (ESPECIALLY delivery, but not relevant to OP). Microsoft runs email servers better than you can, and for cheaper. > "Cloud" is nice, but it still needs to be managed I guarantee you are spending significantly less time managing M365 than anyone ever has managing on-premise exchange. I haven't even brought up SQL because literally anyone who has ever dealt with an SQL issue will tell you that they never want to manage a SQL server again. Any of the big 3 cloud providers will run a database better than any of us ever could, especially when it comes to pricing after you include your salary. Unless you know of some secret way to set up an automatic geo-redundant SQL server with automated tested backups and 24/7 on call support engineers (bare minimum for mission-critical workloads) for less than 500 bucks a month, hosting it yourself will always be worse.

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someguy7710@reddit

I don't know what you are doing with exchange. But most management is done with the same shit you do with ms365. Our uptime was similar to 365. Sql availability groups work great. I guess it depends on your uptime requirements. So not smoking anything except stuff I grow myself thank you

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rootbeerdan@reddit

> most management is done with the same shit you do with ms365 Most of us don't have the leisure to ignore maintenance and security requirements > Sql availability groups work great. Until they don't

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someguy7710@reddit

Fine argue with me all you want. I update on time every time. We have monitoring for when things break, but like I said, it doesn't really happen all that often. "Until they don't" yeah no shit, everything works great until it doesn't. I wouldn't have a job if everything was candy and roses. This. is. why. we. have. a job. Fact is we have to work sometimes, and honestly it's what makes my job enjoyable. I get bored when there is nothing to do.

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rootbeerdan@reddit

> This. is. why. we. have. a job. Fact is we have to work Now I know why everyone is miserable in this sub, *this* is what people do at their jobs. I'll stick to the cloud and enjoy my life and larger budget, thanks.

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nbfs-chili@reddit

For me the big advantage of running it in the cloud was it was someone else's problem when it went down. "We called MS, they're working on it" was so much easier than rebuilding servers and restoring from backups.

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someguy7710@reddit

I get that, but it doesn't always satisfy the "boss". So then you are left helpless

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gonewild9676@reddit

Eh, it's one thing to keep the server running, it's another to keep off the myriad of email blacklists so you can actually send email. The getting a spam firewall tweaked. Then add hosting costs, licensing, backups and high availability and DR and it's easier and probably cheaper to throw it over the wall and let Microsoft deal with it. If you use SharePoint, this goes triple, especially with backups.

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wallacehacks@reddit

Not the point.

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DarkAlman@reddit

I can run Exchange in-house I just don't want too lol I'm the type to generally prefer to run everything in house and I'm not a fan of cloud products generally speaking. Maybe I'm old and set in my ways but that's the way I am. But Email is one of those things that it should be easy and Exchange can be monolithic and a giant pain to maintain. I'll maintain my on-prem VMware, AD, and RD servers any day of the week but I was happy to let my Exchange Servers die in a fire.

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ZAFJB@reddit

>Exchange can be monolithic and a giant pain in the ass to maintain for something that should by all rights be easy. Where's the pain in the ass? Setting up a user email account in exchange on-prem is no more difficult that on M365. Maintenance is backup (automated), installing updates (automated) and CUs. CUs are seldom enough and simple enough we run them manually.

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DarkAlman@reddit

CUs can take hours and coming from an MSP where I had to manage a dozen of these things it was a pain in the arse. Patchtoberfest for Exchange meant working evenings for a week While Windows patching was at least automated Exchange is fine when it's working, but when it breaks it's a giant pain. The server requires a lot of hands-on maintenance compared to a lot of other products, and it's no wonder big companies have dedicated Exchange engineers. With 365 I don't have to worry about any of the back end Just mailboxes

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LOLBaltSS@reddit

Yep. I don't miss getting blown up by Mailive at 3 AM and having to unfuckulate a client's busted DAG. When we reached that point where most clients were on 365, a lot of those calls that I'd get went away because all the overnight help desk techs had to do was look at the Office 365 status page and tell the client that "Microsoft is working on it". Licensing was also much easier as well since we could just throw clients on Business Premium and keep them from attempting to buy perpetual office licenses from those shady fly by night sellers that insist that "Microsoft's activation server is down, please send us the phone activation code".

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KaneTW@reddit

I switched from in-house Exchange early-2010s version to 365. Best decision I've ever made.

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adx931@reddit

Maybe pricing has changed in the past couple of years, but last I looked, if you're running exchange, sharepoint, and the required server hardware for that, and everyone has a couple of copies of office for their various devices, Office 365 is cheaper per user over any length of time until you are into the thousand plus user range. Unless you have a specific need for keeping it in-house, it's difficult to to make the business case for it. I say that as a person that is generally anti-cloud.

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wallacehacks@reddit

Not the point at all.

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Cormacolinde@reddit

The biggest problem with On-prem Exchange these days is keeping it secure. but if this is in an offline environment, the pressure isn’t the same.

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RikiWardOG@reddit

I think when it comes to exchange we just all know how much overhead there is with running it on prem. It's just annoying, like running a SharePoint farm. It's not really hard just a pain in the ass

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ZAFJB@reddit

> all know how much overhead there is with running it on prem What overhead? We need AD and DNS anyway. Just need a bit more backup space is all.

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wallacehacks@reddit

I think you overestimate "we" in this context. Odds are I underestimate them though. I feel like a willingness to read documentation and understand how systems work is very rare in a field where it should be the bare minimum.

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bbqwatermelon@reddit

I for one welcome the challenge.

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nmdange@reddit

Read up on the preferred architecture and follow the recommendations when designing your environment: https://learn.microsoft.com/en-us/exchange/plan-and-deploy/deployment-ref/preferred-architecture-2019?view=exchserver-2019

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Photo-Josh@reddit

>This is going to be in an offline environment. Can you elaborate more on what this means? Generally when we say something is an offline enviornment, or "air-gapped ", that's for a very specific, single purpose. For example, a CNC shop might have some very old XP machines that have the drivers/serial ports for their CNC stuff, and it requires absolutely zero connection via a network to any other device to function. However, an Exchange server by definition REQUIRES a connection to other mail/dns servers to do what it's meant to do. If you didn't have a connection to at least another email server (separate domain) then you could only send emails within your domain... which honestly seems kinda useless.

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Klynn7@reddit

My money is it’s a defense contractor operating on a classified network. It’s fairly common for them to use Exchange for email to other organizations on the network, but it’s not internet connected (so M365 is out).

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havntmadeityet@reddit (OP)

Bingo

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DertyCajun@reddit

Does this satisfy some CMMC requirement?

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Klynn7@reddit

CMMC pertains to unclassified (generally online) systems.

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Mantly@reddit

Dang this sounds like fun!

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FilthyCloudAdmin@reddit

At that point u might as well just use teams instead of mail if this is indeed the case.

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asailor4you@reddit

You can’t run Teams on prem, so it’s not an option for air gapped networks.

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etzel1200@reddit

Can you point me to the Teams server install?

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havntmadeityet@reddit (OP)

It’s a classified WAN. The users want more ways to communicate and collaborate. Currently we’re just using Atlassian tools and shared folders which make it difficult to communicate when they are in a closed space.

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RoboNerdOK@reddit

You might look into offerings from DISA, depending on which classification / network you’re on. DEOS or CESO might be right up your alley if you can get approval for the monthly per-user fees. It’s paid via working capital funds so it’s a lot easier to whip out a charge card rather than having to cough out a MIPR.

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xxdcmast@reddit

Not necessarily, especially since OP states military. I am going to guess that this may be for the militaty or defense contractor. If that is the case "offline" could encompass a large network, across physical location, simply with no access to the internet. They may be using exchange to allow communications within different locations of their "offline" network. Its not as uncommon as you think.

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dnuohxof-1@reddit

Yea the offline bit is a little confusing…. If it’s air-gapped there’s plenty of other better solutions for internal messaging

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Blue_Sky311@reddit

If you do 365 then you already know what you are going to do in exchange because it is the same, if you are going to keep some part on cloud and other on prem then you will need azure/entra directory connector

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Oceanwave88@reddit

I ran exchange in-house for 20+ years and it was great I left and went to an organization that had 365 and I know it was because I was used to in-house, but 365 was problematic with outages. The organization I left got a cheap remote hack to replace me and he moved the organization to 365 with no planning and my inside sources say they are now over a year in and the mail is still all screwed up and not working properly.

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johnwicked4@reddit

some things are better to own and run, others are better for the cloud leave email to the experts and the cloud, pay them for the damn service (o365 etc) as it adheres to every security, financial, government and medical law/governance/legal/iso requirement

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ZAFJB@reddit

Sigh, go and read *and comprehend* the OP. Online is *not* an option.

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johnwicked4@reddit

the post was edited to include that later

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thank_burdell@reddit

I used to joke that exchange is a pretty great system as long as you don’t try to send email through it. In all seriousness, it’s one of the better groupware systems out there for contact management, calendaring, and internal messaging with auditability. And it’s that auditability and local storage that makes it attractive for things like confidential email that can’t be trusted on a cloud based provider. I don’t like MS stuff in general, but exchange was actually one of their better products.

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ex800@reddit

Use DAGs and load balancers Replicate via DAG (three is a good number) and automate the deployment process as much as possible as the simplest way to not have to cope with borked Exchange updates, is never update a live Exchange server, spin up a new one on the most recent build, update it, add to DAG, replicate, and decom the old, rinse and repeat... Whether you go for distributed, or centralised should be driven by bandwidth between the sites, not because there is space to have a local server. Lagged copies can be nice, but not an alternative to having a proper backup (VSS of VM is simplest). Litigation hold makes for an increase in storage requirements, having an archiving platform can be significantly better depending on size of environment (how may mailboxes of what expected size after "staff lifetime"). Any archiving platform should use a file or object store for storage of attachments, one that only uses SQL does not scale well... Have a method for exporting "leavers", simplest is export to PST and store as per any other file. Using internal PKI (Windows cert services are fine) is much simpler long term than using self signed certs.

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catherder9000@reddit

Offline tip. Make sure you configure everything for offline use, if there is no internet access there are some things that Exchange will fail to start or time out during startup because it can't find CRL and CryptoAPI. https://techcommunity.microsoft.com/t5/exchange-team-blog/configuring-exchange-servers-without-internet-access/ba-p/593692 There is a bit of extra reading you will want to do, but everything works the same as cloud based (almost everything).

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Cormacolinde@reddit

This! CRL checking can cause a lot of issues with offline environments.

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Shining_prox@reddit

Just straight up fight to NOT do this. Take data on costs, security nightmare, management time wasted…

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imrik_of_caledor@reddit

If you have the capacity, build it as a DAG so you can update it in hours, unless you really enjoy spending all weekend installing Exchange updates.

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Commercial_Papaya_79@reddit

it sucks, just make sure dns is working well. i just came from an airgapped env with 3 diff on prem exchange envs. then again im not an exchange person.

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fargenable@reddit

Probably want to put some type of spam/content filtering appliance in front of it.

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renderbender1@reddit

For an airgapped environment? 👀

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fargenable@reddit

No, just to limit spam.

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JerRatt1980@reddit

Just use any best practices site that gives you a step by step. It's not hard at all, especially in today's day and age, where the setup nearly takes care of everything for you. But it's always good to at least learn about where to place log and database locations, database configuration for future planning, things like retention policies, quotas, archive, etc. Going through everything in ECP and at least read up on the options and use of each section will just about cover it.

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Dolapevich@reddit

I would docker-compose up something else. Eg:\ https://github.com/docker-mailserver/docker-mailserver

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ThanksForPIaying@reddit

Have you looked into the Client Access Licenses yet? When I last checked a few years back, you could only buy them in blocks of 5 + 10 thousand seats.

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DramaFreSinceTomorow@reddit

I’m weirdly envious of you. I was hired about 15 years ago to do that same thing. But now my job has morphed that I barely touch Exchange at all. I kind of miss it. :( But yea, easy peasy. There’s a ton of good docs out there if you get stuck. Sounds like you won’t be forward facing, so even easier on you.

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countvracula@reddit

Not at all difficult bud. Will just a bit of studying. If you understand basic mail flow the rest will reveal itself to you as you make changes and stuff https://www.alitajran.com/install-exchange-server-gui/

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occasional_cynic@reddit

Yup. Microsoft has simplified Exchange a great deal since Exchange 2010 (amazing what happens when they have to run in themselves). Just please make sure you have some redundancy.

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Dusty_One57@reddit

DAGs and multiple exchange servers are good for redundancy

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graph_worlok@reddit

If your work is spinning up a network like that which they can truly state is isolated from the internet, then they should be able to solve this

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EVERGREEN619@reddit

What a nightmare, I just decommissioned some old exchange server and stood up hmail instead. Its working for me nicely. Hmail is a free open source tool from Microsoft that provides emails. You should check it out as a possible alternative to exchange.

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jackoftradesnh@reddit

Why exchange and not something open source? Considering the use something more simple seems appropriate. I’m my experience, supporting a Microsoft product is more or less giving yourself job security. As in - lots of info is required to operate, troubleshoot, and repair it during production - compared to something more simple built from the ground up (postfix/dovecot/frontend of your choice).

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robbzilla@reddit

It shouldn't be too hard, unless they had an Exchange environment in the past. I found that out the hard way once... That can be a nightmare.

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SilentPirate@reddit

There are Gov/DOD-safe offerings for M365, you might want to look at that even if you only use the Exchange Online stuff and ignore everything else. Maintaining compliance at that level for a DIY Exchange setup is going to be a handful. It also means that you never need to patch your Exchange servers or worry about database redundancy settings etc.

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ZAFJB@reddit

> Maintaining compliance at that level for a DIY Exchange setup is going to be a handful Why?

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Turbulent-Pea-8826@reddit

It can be done but it might be a struggle to maintain with 3 sysadmins. My advice is whatever proposal you set forth try to include another sys admin in the budget. It might not get approved but it never hurts to ask.

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ZAFJB@reddit

One sysadmin can happily manage an Exchange server if necessary. One sysadmin is never a great idea, but the reason for that is never Exchange server in itself.

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oaomcg@reddit

and... how do you plan to send email in this "offline environment"?

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ZAFJB@reddit

From one workstation to another both connected to the same offline environment. Simples!

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MasseMasovic@reddit

Our developers wanted the same thing for testing purposes, and told us that it was "easy" to setup. Sure, but they missed that they would need an Active Directory and all that comes with to get the correct setup for their testing. Don't forget about all the systems around exchange.

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ZAFJB@reddit

Exchange needs AD and DNS Trivial to setup. Can be done in about a day, or less.

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hunterkll@reddit

>Don't forget about all the systems around exchange. Besides AD, what other systems? Because AD is all you need. Well, and an exchange aware backup system or native protection configured.

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MasseMasovic@reddit

In our case it's the entire infrastructure since we don't want them on the same network as our prod/staging/test. Networking, Backup (or atleast the ability to reset an rollback). There's a need to setup MX-pointers and other dns-records.

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vv1n@reddit

Go for exchange online if possible.

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ZAFJB@reddit

You should read **and comprehend** the OP.

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p38fln@reddit

In a totally isolated environment it's not that hard to spin up, there's a setup program that walks you through the steps. It's tightly integrated with AD. If you don't use AD, you can't use on premise Exchange. Your internal DNS also needs to work properly and you'll have to set up the autodiscover settings on your private network, newer versions of Outlook simply won't work properly if you try to manually configure it.

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FilthyCloudAdmin@reddit

When you say offline i assume u mean not cloud. Cause an exchange server needs to be online. Is it hard. No. Its very easy. You should have it up and running in a week.

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hunterkll@reddit

>When you say offline i assume u mean not cloud. Cause an exchange server needs to be online. It absolutely doesn't. We have several airgapped deployments of exchange. It's for internal messaging, calendaring, and room reservation stuff on that network that can't be internet connected, but spans several sites.

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FilthyCloudAdmin@reddit

Sounds horrible.

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hunterkll@reddit

Horrible? Exchange is pretty much set it and forget it. I've helped set up a few, and since Exchange 2013 was released, don't dread exchange management anymore. Before 2013 you couldn't pay me enough.  FWIW, we're a fortune 100 sized company, that has a lot of different unique and security requirement environments. Both internal and customers. You're not using cloud email on some of these systems... [https://upload.wikimedia.org/wikipedia/commons/6/6f/Intel\_GreenDoor.jpg](https://upload.wikimedia.org/wikipedia/commons/6/6f/Intel_GreenDoor.jpg)  But yea, on-prem exchange is much nicer and easier to manage in my experience than O365, and with better uptime and control... company wide we still maintain exchange clusters for VIP users and critical systems.... to protect against O365 issues. Bulk of the rank and file is on O365 however.  Shit, I run hybrid exchange 2019 at home myself for a large variety of reasons (including some hilarious fish tank integration with exchange and SCOM, and having a local SMTP relay), zero maintenance required except occasionally applying the latest CU.....

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FilthyCloudAdmin@reddit

All good if u wanna use onsite exchange. I would rather not. It has improved a lot over the years tho. Used all versions from 2003 to 2019.

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ZAFJB@reddit

> All good if u wanna use onsite exchange. Did you actually read the OP?

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hunterkll@reddit

>I personally dont see the point of air gapping an exchange server like this but i dont know your enviroment. Im sure there was a reason to that madness. The entire network is airgapped. As in, everything being done there - file servers, applications, development work, etc - is all on that network. There's zero internet connection (or if there is one, extremely locked down/filtered - no cloud services, no data exfil potential stuff, just limited to extremely just what is needed).  It's not just the exchange server that's airgapped. It's all the workstations, servers, users, etc.

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FilthyCloudAdmin@reddit

Yes thats enviroment isnt my thing. It sounds very legacy. Good luck sir.

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hunterkll@reddit

Legacy? LOL! Half of them are new deployments - 2015 and newer. It's high security environments.  Microsoft isn't trying to ditch onsite exchange, they've firmly committed to supporting it. But they're adjusting the cost to be the same as O365

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FilthyCloudAdmin@reddit

https://learn.microsoft.com/en-us/lifecycle/products/exchange-server-2019

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hunterkll@reddit

[https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-server-roadmap-update/ba-p/3421389](https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-server-roadmap-update/ba-p/3421389)  I can provide links too! Except mine's stating the release plan for the next version of exchange!  We have moved the release date for the next version of Exchange Server to the second half of 2025. The next version will require Server and CAL licenses and will be accessible only to customers with Software Assurance, similar to the SharePoint Server and Project Server Subscription Editions. We will provide more details on naming, features, requirements, and pricing in the first half of 2024.  We will maintain the current support dates for [Exchange Server 2013](https://docs.microsoft.com/lifecycle/products/exchange-server-2013), [Exchange Server 2016](https://docs.microsoft.com/lifecycle/products/exchange-server-2016), and [Exchange Server 2019](https://docs.microsoft.com/lifecycle/products/exchange-server-2019); however, **we plan to support the next version of Exchange Server beyond October 14, 2025. We are moving the next version of Exchange Server to our** [**Modern Lifecycle Policy**](https://docs.microsoft.com/lifecycle/policies/modern), which has no end of support dates. We plan on continuing to support Exchange Server as long as there is substantive market demand.  and....  A key element of the Exchange Server roadmap is our investment plans for Exchange Server 2019, which we are excited to share with you today. Over the coming months and years, we will be adding features to Exchange Server 2019, and we’ll continue to support regulatory and data privacy requirements. Our continued investment in Exchange Server 2019 allows us to deliver improved security, deployment and management capabilities, and reliability—the attributes our customers tell us they need most from Exchange Server.  So yes, 2019 has an EOL. So what? The plan's been communicated.

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FilthyCloudAdmin@reddit

Hey man u do you. Enjoy exchange.

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cmoose2@reddit

Legacy? Are you 15 or something?

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FilthyCloudAdmin@reddit

Microsoft trying to ditch onsite exchange. U prob think GPOs and active directory are also not legacy.

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FartInTheLocker@reddit

Sounds like the secure setup for their required usecase? I assume you'd just allow all incoming and outgoing connections to the server and call it a day.

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FilthyCloudAdmin@reddit

I wouldnt work at a place with this setup.

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FartInTheLocker@reddit

Bit of simple networking scares you off?

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Klynn7@reddit

I almost feel like he’s a novelty account doing a bit of being the “filthy cloud admin.”

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ottdriverssuck@reddit

The cloud portal clickers are afraid of doing some real networking work.

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hunterkll@reddit

Right? I mean... it's not exactly rocket science. Some uses cases cannot allow internet connectivity but have a large network footprint with many workstations. What are you going to do, not have a collaboration system?

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FartInTheLocker@reddit

Yeah I'm not sure, I get Exchange on-Prem is old-school, but there's a reason MS is still supporting it. There's plenty of companies that CANNOT store email data in cloud, it seems that just because some admins haven't worked in those places, they're therefore not valid requirements.

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FilthyCloudAdmin@reddit

No. Dont want to work in a legacy enviroment.

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Scary_Confection7794@reddit

I remember when my lovely exchange 2016 server was bricked by a cu. That was a joyful way to spend a Friday evening lol. Now I am riding the exchange online wave :)

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ZAFJB@reddit

> I remember when my lovely exchange 2016 server was bricked by a cu. I remember when our Exchange server was bricked by something. Failed over to the replica VM, and carried on. We lost about 10 emails.

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FilthyCloudAdmin@reddit

This is the way.

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ZAFJB@reddit

> Cause an exchange server needs to be online. It does not

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DarkAlman@reddit

https://www.alitajran.com/exchange/ Ali Tarjan is your friend

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shiftypugs@reddit

Why are you not using your fielded stuff or asking someone with fielded stuff to provide email for you?

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mark_rees@reddit

I last setup Exchange 2016 and it's not bad manage. Not having it connected to the internet would make it even easier. The only things I can think of that were obnoxious is to make sure you have plenty of disk space on all drives. Exchange does a lot of logging and if the free storage space drops below a percentage of the total drive Exchange will just stop delivery mail to mailboxes. If I remember right, I also used ReFS for the drive with the mail store. Most of the administration you'll do will be through Active Directory. Exchange will update the schema of your AD, so make sure you have adequate privileges when you set it up.

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tarentules@reddit

We run exchange where I work. I am the one that primarily controls it and don't really have any major issues with it. If you don't know Powershell, I highly recommend you start learning as it will be your main tool with running exchange, or at least it is for me. The web console/GUI is fine for the basic stuff b,t there is a lot you can do on/with exchange that only exists behind the exchange management shell (powershell console on the exchange server).

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nighthawke75@reddit

If it's a military contractor and everything's going to be mil-spec level security, I'd suggest bringing in a security consultant to help set things up and operations.

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BadSausageFactory@reddit

offline exchange server there's so much to unpack there. other people have offered some really good comments but I just want to ask why you need an email server that isn't going to connect to the internet. commune? secret society? malware research?

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Klynn7@reddit

Likely defense contractor. Classified networks use Exchange but no internet.

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BadSausageFactory@reddit

secret society, then. called it.

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kaziuma@reddit

OP, you need to clarify what 'offline environment' means and what kind of other variables are in play here. It's causing a lot of confusion in the comments.

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cmoose2@reddit

People in these comments just don't have as much experience as they pretend they do.

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kaziuma@reddit

Seeing so many people spouting off solutions without knowing these details is worrying.

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occasional_cynic@reddit

Most people here just parrot Microsoft talking points. And many are HelpDesk only.

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MeanFold5714@reddit

I'd wager most of them have never even encountered a network that wasn't connected to the internet, much less had to do sysadmin work on one. It's kind of jarring to see the confusion on display.

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meatbeater@reddit

Welcome to Reddit, experts in every possible subject that have zero knowledge

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Kimyaaaaas@reddit

I ain't sure if it's a good place to ask, but i was actually looking to get to know more about exchange and what it actually is, since i'm looking for a technical support job in microsoft and it requires good understanding of exchange, i'm still searching about it but this subreddit came up and would be great if someone guides me where to fully grasp what it actually is and why it does already exist, any idea where i could start from? i just thought that you guys seem to have a good basis of what exchange actually is

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cspotme2@reddit

Offline environment for what? I can't fathom what a offline exchange environment is going to do for mail flow. Maybe all you need is a smtp service.

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Klynn7@reddit

Probably classified work.

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jackmorganshots@reddit

Setup? Bring your a game, no need to quit drinking tho. Securing it on the other hand...

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davidsinnergeek@reddit

Mike, is that you?

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Virtual_Ordinary_119@reddit

I due It for my fomer company, I was the only sysadmin and I had experience regarding mailservers only on the Unix side. I due it without headaches, like 5 years ago, and it's still running fine ad far as i know. 2 hints: - learm and love powershell - pit a third party antispam in front of it (we used Cisco ESA)

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Bordone69@reddit

We’re sunsetting ours…. Today. Powershell (which all MS admins should know how to find what they need to do). Good luck!

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DeerEnvironmental544@reddit

Postfix? Yikes thatl b fun I guess

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ComGuards@reddit

Even though the exam has been retired, if you can find a used copy of [Paul Cunningham's 70-345 book](https://www.amazon.com/70-345-Designing-Deploying-Microsoft-Exchange-ebook/dp/B01LHSV9ZS/ref=sr_1_1?keywords=paul+cunningham+exchange+2016&sr=8-1), it will be useful information to have.  And [Practical365](https://practical365.com/exchange-server/) should be in your bookmarks =).

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