Exchange. Help.

March 3, 2006 3:59 PM

So, looks like I'm going to Exchange. I think it's crap, am I wrong?

It has been decreed that we are to move to Exchange. We currently use a standard Linux mail server and I use Thunderbird. It has also been decreed that we all have to use Outlook. This is, and I quote, "not negotiable".

Fortunately, we do have a Windows 2000 server with a live IP address that will probably be the host. I'm hoping that I can setup IMAP access for those times that neither Outlook nor IE are availlable.

I'm impressed by the web interface though. My reaction has been to grab IT Tab for Firefox, with the intention of using it at my desk instead of Outlook.

So, several questions;

* Is Exchange technically crap, or just really, really overpriced?
* Is IIS still a massive security nightmare?
* Is the Outlook Web Access system fast enough to use as a primary client?
* Will the current version of Exchange, plus the Web Access server stuff, run on a Windows 2000 server?
* Will the current version of Exchange play with Outlook XP, or will the company also need to buy Office 2003 for everyone?

posted by krisjohn to computers & internet (19 comments total)

In my opinion, companies that use Exchange Server are those that have shitty/lazy IT departments who do not take the time to understand how to run an enterprise-level Linuxbased mail server.

If your Exchange administrator is not that good and you are asking too much of your Exchange server, expect many instances of downtime, lost mail and other problems that plague overloaded Exchagne servers with crappy admins.
posted by camworld at 4:02 PM on March 3, 2006

Outlook Web Access + Firefox = bad, in my experience. It only seems to have full functionality in IE.
posted by restless_nomad at 4:08 PM on March 3, 2006

- I don't mind Exchange if it's administered properly. I've seen some really messy implementations that created a terrible experience for everyone involved. It's remarkably overpriced but if your PHB is saying that's where you're going, it's not the end of the world.

- IIS is still very much an inferior web server. I think they've cleaned up their act a bit in terms of security but I still dislike it for a number of other reasons.

- OWA in my opinion is not fast enough to use as a primary client

- Yes

- I still have some Outlook 97 clients lingering around the company and we're at Exchange 2003. Outlook XP will be fine.


Bottom line: it's not as bad as you think.
posted by saraswati at 4:08 PM on March 3, 2006

Of all Microsoft's software, Exchange is probably the best. The big downside to Exchange is, of course, that it's totally proprietary, expensive to buy, and expensive to upgrade. And it is challenging to script... I find the scripting available in Unix tools to be far, far better. I wouldn't use it, myself... but overall, it's not too bad.

It will support IMAP, so you should be able to use whatever client you want. Do you know why they're decreeing that you must use Outlook?
posted by Malor at 4:08 PM on March 3, 2006

Or, there are some sales droids that have managed to get their 'overwhelming need for a fully functional calendar solution' into place. Usually these are the same dicks that feel they're not man enough if they don't have Microsoft Outlook taking over their lives.

I think Exchange is crap for most places. Some larger enterprises actually use a lot of the features that it comes with, but for smaller shops, it's totally bloated overkill. It is decent if you want to keep everyones mail on the server so you can play "I am the EMAIL GOD!" and do fun shit like recall messages and delete crap from users inboxes.
Mostly it's shuffled into play because lazy people want to 'standardize' on Outlook because they know nothing else and don't want to feel like they're missing out on 'real world' skills.

IIS is still a security hole, especially so on Windows 2000. It's waaa better on Windows Server 2003, but.. well, it's still IIS. OWA is slick, but like many other web based mail thingies, gets bogged down.
Exchange 2003 will run OK on Windows 2000 Server. Just give it LOTS of CPU and *LOTS* of RAM. Also make damn sure the box is redundant. RAID 5 (6 if you can) minimum. Restoring dead Exchange boxes is a nightmare.
And I dunno about needing Office 2003, but to take advantage of some of the newer features, I think you need the newest Outlook.
posted by drstein at 4:09 PM on March 3, 2006

Exchange is like most other software products: it's as good as it is managed. That's pretty much the bottom line.
posted by xmutex at 4:24 PM on March 3, 2006

A lot of sizable mail operations run on Exchange. Tellingly, HotMail doesn't...:-) Yet.

That said, I've worked with many mail systems, including Lotus/Domino and Exchange on Windows, and postfix, Exim, and sendmail on Linux, and some others on other platforms. They all have their strengths and weaknesses.

The key issues for a successful Exchange operation are having a database server for Exchange that it is up to snuff, and as reliable as you can make it, and then installing and using approved backup, anti-virus, and support utilities. You have to be sure to stay ahead of mail volume on upgrades, and routinely make sure you can bring the system back from any conceivable failure, because Exchange systems are inherently targets for more script kiddies than most any other system, save Sendmail.

Also, as a system built on an RDBMS, Exchange is unforgiving of any problem in the data store, so you need to have journaling enabled, and transaction logging going, if your site gets a significant volume of messaging, or if you begin to build workflow applications on top of messaging. Otherwise, coming back from maintenance operations or a major system failure is going to very likely mean lost mail. But in this regard, it is no worse than Lotus/Domino on Windows, and maybe better.

It's also vital that your mail alternates be set up correctly, including alternate MX records in DNS, and hopefully, some kind of secondary upstream spool which can handle inbound deliveries for at least a few hours in case of server problems, so that your system isn't getting whacked as you are trying to recover it, if it should come to that.
posted by paulsc at 4:27 PM on March 3, 2006

Exchange is a lot more than mail - it's the contact and time managment elements that a lot of companies value a lot more than the email.
posted by jedrek at 4:27 PM on March 3, 2006

So you don't really ask a lot of questions where the answers are useful, and it sounds like you're kind of determinted to hate it.

The only things I can usefully contribute is details about Outlook and OWA. I develop an Outlook plugin, so I know some about this.

Outlook XP (aka Outlook 2002) will work fine with the latest Exchange server. Outlook 2003 has a bunch of bug-fixes, some of which only will affect plugins and some of which affect everyone, but the biggest thing you probably would care about is the implementation of a semi-reasonable security model for the scriptable components of Outlook, and the fact that it doesn't load externally linked images by default. Outlook XP was retrofitted to support an approximation of the 2003 security model with SP3, so if you do decide to go with Outlook XP, I would recommend you make sure everyone in your company applies the latest patches.

OWA is quite usable (in IE, dunno about FF), and sometimes I am forced to use it when I want to read mail while debugging my plugin. It may not be as snappy as OL for some things, and with popup blockers I've had it once eat a message I was writing, but there are some things that it's way better than Outlook at (try deleting 140,000 messages with Outlook. Let me know when it's done). I personaly prefer outlook though.

Good luck!
posted by aubilenon at 4:30 PM on March 3, 2006

Pure IMAP: works like charm, but no calendar/scheduling thingies.

OWA in Firefox: sucks big time.

OWA in IE: bearable, but you have to use crappy IE.

Outlook: quite usable actually.
posted by cerbous at 5:42 PM on March 3, 2006

The key issues for a successful Exchange operation are having a database server for Exchange that it is up to snuff

Which is the key point, and key problem. Everything lives in those databases, and if they get trashed, you'll get pointed to the Standard Database Fix.¹

In my nowhere near humble opinion, email is far too important to trust to a database, but that's just me.

So. You'll want to spec good hardware, and be religious about backups -- and don't get rid of that Linux box. ². You'll want to do your spam filtering and virus checking on that box, then pass clean data to the Exchange box. The more things trying to monkey with the datastore, the more likely you are to lose it, so keep the filtering out front, and let the Exchange server do just that.

And, for the record, a massive datastore collapse is usually how you get Exchange out of the company. I'm not suggesting, I'm just saying, ya know.

Oh, yeah -- circular logging is always evil, but it is very evil when Exchange is involved. If you don't have enough disk for sequential logs, fix your backup routine, if you still don't have enough, go buy more, disk is cheap, even FC disks in a SAN, compared to the massive lossage circular logging will cause.

Speaking of which, a SAN can be very handy here -- not that'd I'm doing rolling snapshots or clones every eight hours. Yet.

Finally: Quotefix for Outlook. You already know why you need it.

¹ Restore from backup. In early versions of Oracle, which rarely ate an entire database, but loved to eat tables, this was "drop table, restore from tape." Yes, there are utilities that claim to resurrect damaged databases. They almost always lie. Backups are your one true friend, and you'll want both brick and store level -- brick level for user unbars, store level for major database splats.

² Unless you are going to replace it with a real OS, like FreeBSD: By Elitist Pigs, For Elitist Pigs. We've already established I'm not humble
posted by eriko at 6:48 PM on March 3, 2006

Yes, you are wrong.
Exchange is not inherently crap.
It is not, however, very tolerant of inadequate care, and rarely survives the "Stick the mail-server in the closet and forget about it for 12 months at a time" school of systems administration.
posted by madajb at 7:11 PM on March 3, 2006

I'm not clear on whether you're asking from a user perspective, or if you will have a hand in administering the server. I was at a start up that had an Exchange server on NT 4. I took over administration of it, and it was terrible. Mostly because of Outlook being unable to handle large mailboxes and often corrupting the .pst file where it stores the mail locally. But also, the server itself drove me crazy just because of the lack of useful errors or options. When it breaks, and you can't figure out why and there's no option in the gui for what you want to do, you'll be aching to be back on the linux box really quickly.

We switched over to Cyrus imap and everything was fine for a few years. By then they had grown to a point where they had a sizable sales team. Word came down from on high that we would be getting an Exchange server. It was actually announced at an all-staff meeting. The sales team literally cheered, while the engineers just looked on with utter confusion. The sales people thought of it as some kind of a graduation to big company status. No one had any problem with their email up to that point, but they knew what everyone else used must be better.

In my situation, I was able to to tell them simply that I wouldn't install it. I instead got them quotes from a few contractors on what the total cost would be to have them come in get it up an running, and what the yearly cost would be from then on. To have the same functionality that we already had for free. Never heard about it again.

At any rate, if it must be done, do NOT put it on a public IP address. Keep it inside the lan at all times. It can run an IMAP server, so you can use whatever client you want. The problem is most likely that they are going to use it for calendaring, and there's no way to do that without Outlook. OWA is pretty slick, though. You will have to use IE for it to work properly. That's my real problem with Exchange. Even if you do have it running flawlessly, you pretty much have to go MS across the board. For it to function as advertised, you need to be running a domain for logins and use active directory for name services, an use Outlook and IE on the desktop. Somehow that doesn't seem to bother some people.
posted by team lowkey at 7:41 PM on March 3, 2006

I have daily experience with an Exchange server in an Active Directory environment, supporting a couple hundred users, so I can offer a little practical advice.

Your questions, in a nutshell: Exchange is most emphatically not crap, IIS sucks (though I wouldn't necessarily call it a nightmare), OWA works really well but I'd use Outlook when possible, Exchange Server 2003 is supported on Windows Server 2000, and Outlook XP will be fine (as will mixing XP and 2003).

That said, Exchange is not sendmail/qmail/whatevermail, and Windows Server is not Linux. If you're exposing an Exchange server directly to the internet, you'll want a hardware firewall in front of it.

You'll want anti-virus software on it, properly configured -- it must not be allowed to scan the Exchange store or journal/log files, or your performance will blow. It should also be able to hook into Exchange's mail delivery systems, and scan your incoming and outgoing email. You'll probably want something that'll do spam filtering, too.

Incidentally, you might offer a compromise. At my company, mail from the Internet first gets delivered to a Unix server, which takes care of both antivirus scanning and SpamAssassin. Anything that gets past those filters is delivered to our Exchange server.

Internal email, of course, is delivered directly to Exchange. Outgoing email is passed to the Unix server from Exchange, and gets virus-scanned, but skips SpamAssassin.

We allow access to OWA from the Internet, but not to IMAP, POP3, or Outlook connections. You need to connect to our VPN for that. You can open up whichever ports you like, of course.

Finally, are you using Active Directory right now? If not, now is the time to start. Not only does it make Exchange happy, but there is no better way to manage security on a Windows-based network.
posted by CrayDrygu at 7:47 PM on March 3, 2006

Hey if you're buying Exchange 2003, it will come with Outlook 2003 - and I personally think there are great usability features in it.

OWA is spectacularly good at talking to Entourage, if you have any Mac users. Best of both worlds, sort of.

Other than that I join the chorus of "it's not crap if you're not lazy, otherwise, yes, it will be crap" and etc.

Also, make good darn sure you set up reverse DNS on your IP address or email delivery to domains that check for it will not accept mail from you, you spammer, you.
posted by disclaimer at 8:15 PM on March 3, 2006

disclaimer speaks teh truth. Be very careful to not wind up with an open relay.

Chances are, you're going to wind up with a Unix box in front of it to handle inbound mail. At least, that's what I've seen..

internet -> postfix box -> exchange.

postfix box rejects all email addressed to invalid users, handles spam filtering and virus filtering. That kind of setup actually works pretty well, and takes a lot of stress off of the network folks.
Some joints even route *outbound* email through said postfix box too, using a second Postfix instance. That works too.
posted by drstein at 11:16 PM on March 3, 2006

One of the reasons Exchange has reputation for being something of a dog, performance wise, is that when it comes to I/O, virtually all 32 bit versions of Windows servers are poor performers, thanks to the antiquated Scsiport architecture. If this is going to be a mission critical system, it would make a lot of sense to me to avoid just plopping it on some randomly selected Win2K box, and actually setting up a properly specified Win2K3 64 bit box, which will have far better I/O performance thanks to the new Storport internal architecture.

Also, if you are going to do any form of RAID, do not do it in software, or with Windows Dynamic Disks. The combination of Windows 2000 and Exchange will normally force all writes to be completed to the disk platters (unless you implement a special hotfix and setup procedure), completely negating any form of writeback caching the disk controllers or onboard disk caches offer. This is particularly problematic for IDE and SATA disks, which have limited abilities to re-order commands anyway, and will make even fast 15K SCSI disks seem pretty slow. For decent, stable Exchange performance, you need plenty of disk arms, and if you are going to do RAID, you need a caching RAID controller that can work effectively with the default 4K
Exchange cluster size (effective at handling thousands of outstanding I/O requests, for an operation of several hundred concurrent users, using messaging, calendar, and other functions). Journaling should run on it's own disks.

If this is your first Exchange setup, and you don't have the time to go through all the pre-planning documents, I agree with suggestions upthread to get an experienced Exchange consultant involved in setting this up. I also agree about the suggestions for outboard preprocessors, but you still have to have anti-virus and other utilities running on all Exchange machines.

Commit yourself to making this work, and it can actually be a fairly interesting learning exercise, and another resume point to boot.
posted by paulsc at 5:15 AM on March 4, 2006

Thank you, everyone. I feel much more confident that I can minimise disruption to my staff now. I also know that the idea that the only cost will be for the Exchange software is seriously misguided. I'll prepare a budget for RAM and backup upgrades, as well as consultants to sort out ActiveDirectory and the initial Exchange install.
posted by krisjohn at 6:08 AM on March 4, 2006

We've never had any down time with it at my firm. Works great for us, and syncs real well with Blackberry exchange server too. But we got a real good tech guy.
posted by Ironmouth at 10:43 AM on March 4, 2006