Microsoft Outlook: Destined for the Dumpster

I am writing this post about a program that is destined for the dumpster: Outlook. Just like the titans of the past, Outlook too will soon be done for. Here in this article I go over 10 reasons why Outlook is done for, and why I believe Outlook is the forgotten child of the Microsoft Office Suite.

First, some history. I, like many IT helpdesk support agents, have grew up with Outlook. For years, Outlook was really the only sure-fire way to get your email from the late 90’s until the widespread adoption of web-based email clients. The first version of Outlook I can remember servicing at the time was Outlook 1997, which seemed to be way ahead of its time. The silver bullets to any Outlook problems was our trusty ScanPST.exe tool, and Nirsoft’s Nk2edit tool. The authors of these tools forever have my gratitude and debt. Hats off to you guys. Flash forward to 2018, and Outlook is nothing more than a broken down Plymouth van. Outlook has grown to be ugly, slow, and loaded with problems. Sure, like the Plymouth van, it still runs, but, just because something still limps along doesn’t make it an effective means of transport.

Reason #1) Outlook can’t handle today’s emails:

Yes, I’m looking at you, Microsoft. Emails are more than just kilobytes of data now. The web is alive, attachments are large, and emails are heavy briefcases stuffed with assets now. Gone are the days of tiny, efficient emails. Ever try to search in a 25GB+ PST file? (More on this later) The more emails you have, the worse Outlook becomes. Sure, if you run exchange or an Azure hosted exchange server, Outlook chugs fine. My theory behind this is much like Outlook.com – Exchange is doing the bulk of the work handling and maintaining data files, which causes much less things to break. But, for the 98% of SMBs who do not run exchange, Outlook is a dead horse. In 1997 when having a 1gb hard disk was an amazing feat, Outlook was great. It was built for that era. Not so much anymore.

Reason #2) 50GB message store limit.

Outlook has a 50GB data file limit on PST files. (and .OSTs?) Ok, now I know what you are thinking – archive into several data files and tuck these away. And, you’d be right. However, this creates an outright nightmare for management of files, protection of these emails from being deleted by an end user, and searching of emails. While Microsoft knows about this problem, Outlook is not configured out of the box to search across all PSTs that are added into Outlook. See image below for the default configuration. How about searching everything Outlook?

Reason #3) IT admins – I think we all can agree: NK2 or steamautocomplete.dat. What a s&*% show.

For those who have no idea, streamautocomplete.dat (or .NK2 in older Outlook versions) was a place to store nicknames. This nickname file controls what you see the in name dropdown when composing an email. Separate from your contact list, this little bugger of a file does not make it upon migration of PST files to a new PC. In fact, it never will. You’ll have to use NK2edit from Nirsoft, do some song and dance to restore the file with all the entries. It’s a bit of a process:

Listen to end user start Outlook and freak out because no one can remember email addresses. (fair)

Log into system and wonder why Outlook didn’t transfer the nicknames.

Realize (If you’re new to this) that the PST file should hold these entries, but doesn’t.

Copy old autocomplete file into Appdata, a place where files should never live in a production environment (And you can’t change the default location)

Clear old autocomplete file from Appdata.

Open Outlook, confirm autocomplete is clear.

Send 1 email to any email address

Close Outlook

Open Outlook, confirm only one address is in the nickname dropdown

Close outlook and end all processes.

Use Nirsoft’s NK2edit to copy entries to current autocomplete file. Overwrite the file

Open Outlook, confirm all entries are there.

Do this to the 50 other PCs in the Office, because Tammy got her autocomplete back, now everyone does too.

Waste an entire week of doing this and chasing your tail.

We’re just getting started. Buckle up kiddos – you’re in for a nostalgic treat.

Reason #4 Welcome to Scanpst.exe)

So it’s a Monday. You have Outlook issues. Microsoft has given you one silver bullet to fix 98% of Outlook’s issues. Welcome to Scanpst.exe

If you’re wondering why you never heard of this, I don’t blame you. You can’t find it under a Windows search (from the start bar, anyhow) and it’s just as old as that Plymouth van I was explaining earlier. It’s so badly integrated with Windows, that this is the default result on Windows 10:

Anyways, once you find your needle in the haystack, here is scanpst.exe

Here is a few problems I have with the 90’s Band-Aid:

Hard to get to.

Freezes when fixing a PST file (Again, Outlook not designed for large data files).

No command line options for this program. So this requires GUI input at all times.

Has not received any updates or improvements since 1997.

Outlook does not automatically run this for you. Instead, Outlook will sit there and freeze uncontrollably until you run to its aid with Scanpst.exe

Reason #5) Random crashes, closes, freezes etc:

This has been an issue from what I can tell from Outlook 2010. Crashing on email forwarding, crashing when adding an email account (Outlook 2013, happens all the time). Freezing on moving emails. Freezing when opening attachments with Outlook addins, freezing because it wants to. The list is endless and no one at Microsoft can figure it out. Welcome to the club.

Reason #6) Poor management and lack of updates for internal features.

Outlook / Office 365 has made some updates to the process of adding email accounts, but we still face several issues. Admins are stuck with our favorite mail applet from the 90’s to configure emails and move around PST files with. Accessible from control panel > mail, this is really the only sure-fire way to configure Outlook in case anything goes wrong. Have an issue with a PST file? PST file moved? Outlook upon open will bark and yak until you fix it. Treat this mail applet as the backdoor to the club that no one wants to go to. Here it is:

What’s better, with Office 365 you cannot fine tune some settings when adding mail accounts to Outlook. Instead, you must circumvent Microsoft’s new way of adding emails and use our 90’s panel to add the accounts / manage accounts instead. It’s a wonderful world.

Reason #7) Nothing to show here bug / search bug

This is noted by Microsoft many times as a bug in Outlook, and it comes and goes every now and then with new versions. Long story short, it comes down to indexing. Outlook has corrupted its own search index, to which you must go outside of Outlook to remove the index and re-catalog it.

Reason #8) Addins:

Often responsible for breaking Outlook consistently, addins are a staple to why Outlook is still around. Long story short, addins are useful but often are first culprit of issues, especially when Outlook updates with Office 365. I’ve fixed several hundreds of configurations from addins like Norton antispam all the way to TeamViewer. It’s a mess.

Reason #9) Not even Microsoft likes desktop Outlook:

This year with the launch of Office (2019?) aka new Office release via Office 365, all the hype surrounded Excel, Word, OneNote etc. Nowhere was Outlook mentioned. New to the table this year was new icons, and new loading screen, and some broke addins. Lovely. If you don’t believe me just look at the import and export tool.

Look familiar? It should. It’s been the same for 20 years. Yes, a staple to this program. Never updated, never improved. Want to import some data into Outlook? It’ll freeze up while you do. Outlook online has gotten all the love, with a totally new refresh and the ability to encrypt emails. Sad day for the old Outlook.

Reason #10) Not even G-suite likes Outlook:

Want to successfully sync email with Gmail? Gsuite? There’s an IMAP limit on purpose. After days of trying to hunt this one down, a Google employee told me what’s what. Google does not officially support IMAP in general, mainly due to the inefficiencies of how the protocol is used with Google’s servers. What’s more, Google gives you a special tool to sync data via MAPI, and uses a hacked up way to integrate with a PST file. Google themselves sets a limit to only 4gb of maximum local storage, saying “Outlook doesn’t work right with large data files”

Yes… Really..

So, there’s 10 reasons why im not a huge fan of desktop Outlook. While this may come off as a rant, I hope someone up above at Microsoft looks at this in depth and listen to us sysadmins. It would do us all a huge favor!

Catch you guys around next time!