Outlook New rant

HCHTech

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Pittsburgh, PA - USA
No real surprises, just venting some frustration. We have a small utility company (rural water) as a client. 6 employees, all previously on IMAP mail from Bluehost. We've been working on them for a while to migrate to M365 and finally got the ok at the end of last month. This should have been an easy job.

Complication #1 - it took 2 weeks to get their tax exempt status properly recognized by our M365 reseller. Sherweb is pretty good in a lot of ways, but this was ridiculous.

Complication #2, the client doesn't have direct control over their DNS. Their website was built and is maintained by a one-guy company who is apparently reselling Bluehost services. All of his clients are controlled through a single login, so he couldn't share that with us, but instead asked that we just give him the needed changes and he would make them. I knew this would slow things down, but I had no idea how much. We setup the MS tenant and asked for the initial verification TXT record a week ago this past Monday. It took him until Saturday evening to input that record, which we couldn't then work with until Monday morning. Wow. I kept the client aware of the impact this was having and it looks like once the dust settles, they are going to move away from this guy's services - so yea for that, I guess. Apparently some direct words were had, and when we asked for the rest of the changes on Monday afternoon, they were in place by Tuesday evening. Better, but still way slower than when you have direct control over the DNS.

Complication #3, All of the employees but 1 were using regular desktop Outlook, so it was merely a job of backing up the email, contacts & calendars to a PST file, creating a new Outlook profile for M365 & them importing the saved PST once they were logged in and 2FA enabled. 1 employee, who was their main field guy only had a laptop, and we had to work by remoting in while he was driving around in his service truck. The laptop had a cellular connection, so as long as he had a good signal, this went ok, but would randomly drop the connection whenever he drove through an area with a bad connection. That was fun.

Complication #4. Service guy had gotten a new laptop in March and had setup his email on New Outlook. IMAP, non-Microsoft account - which cripples the already scant feature set this app has. He had created dozens of folders, and 3 separate calendars with dozens of repeating events off into the future. No exporting email from the app, no exporting or access to the calendars, which are stored locally, but not in a way that you can do anything with the data.

I tried logging into webmail for that old account, and their webmail client didn't support exporting either - and, none of the folders created had synced back up to the server, and of course the calendars didn't either.

I couldn't put the new email in New Outlook either because it was the same email address - you can't have two accounts with the same email going at the same time in one client - no surprise there, I guess.

So in order to get anything at all, I had to create a separate profile in Outlook classic to connect to their old IMAP email (which took a while since I had to stumble onto the exact configuration of ports and encryption settings that would work since their documentation was.....lacking.) Once this was working, I made sure all of the IMAP folders were synced, but obviously only got inbox & sent items, probably less than 50% of the email he wanted.

I broke the bad news that he was going to have to recreate his calendars (and all of the events) and all of his folders, then individually forward each email in each of those folders to himself to get it into Outlook classic where his new email account was. He was less than pleased, but recognized there wasn't much else to be done.

I think I am going to be the last person on earth to switch to New Outlook. I'm just hoping they send me a survey at some point about why I'm dragging my feet. :mad:
 
Why not use a migration tool such as BitTitan or Skykick for this?
 
I think I am going to be the last person on earth to switch to New Outlook.

The problem is not New Outlook, nor is it limited to Outlook at all.

For far too long people have assumed (and that includes some in the IT sphere, more's the pity, and I hasten to add I'm not trying to imply this about you) that "everything email" can be and should be handled and able to be handled from within their chosen email client. This has never been true either for MS-Exchange (except when using Outlook) or IMAP (when using Outlook or a multitude of other clients).

Server side protocols reasonably presume that folders and filtering will occur server side, and be propagated out to the client(s) that connect to it. One should never assume that various email clients communicate with the servers such that either filter/rule creation or folder creation will occur there.

I have been fighting this battle for years, mostly in regard to Gmail, but not only Gmail, that you set up your folder structure (labels, in Google's parlance), and modify it when needed, on the server side: that is, using the Gmail web interface, whether you actually ever read your mail there or not. The same applies for filters.

Then, and only then, can you presume that every client that connects using IMAP will be seeing "exactly the same email world." Otherwise, it's not uncommon to have a nightmare mix of local folders, not intended to be such, as well as rules/filters on the client side. For the former, nothing you do is going to make a local folder appear to all as an IMAP folder does. And it's a ton of fun if filters/rules were set up in an email client that doesn't sync these with the server, and someone goes on vacation and their email client is not running. Nothing gets appropriately filtered while it's not running because it's the client doing the work, even if it happens to be using IMAP (or other cloud-based) folders for the destinations.

Certain things must be set up in certain places, and knowing that and doing it is one of the basic ways to avoid insanity. I won't even think about some of what happens when someone insists on using POP3 protocol. :: shudder ::

But, I will say that Microsoft's decision to act as "middle man" and upload all email, calendar, and contacts to their own server, and to only do so for mail that's less than one year old (at least for free Outlook for Windows) is maddening. I'm facing that now with a client who was unable to deal with their email, at all, during a period of extended illness, and where the majority of their Gmail is not available in Outlook because it's older than one year. We will, of course, doing mass selection and deletion under Gmail webmail to get things cleaned out, eventually.
 
Why not use a migration tool such as BitTitan or Skykick for this?

For large migrations, I do because it saves time. For little ones, it's normally faster to just do them by hand. In this case, though it wouldn't have helped the problem of getting data stuck in New Outlook. Had anyone asked (they never do) when setting things up, I would have recommended against using New Outlook in the first place. The fact that New Outlook even allows you to create and store data in a non-portable format just proves to me that it's still in beta (and that's being charitable) and shouldn't be used by users unaware of its limitations.
 
I had a similar nightmare over the past few weeks.
Insurance company in town...one of the bigger ones. Owner is a life long resident of this little beach town, well connected, and does his own in house IT work. So at best...I was hoping to get a good reference with him by helping him with his migration to 365....and selling him the licenses.

But then...I see how he won't even end up being much of a good client.
*His original email host..."RackSpace". Heh...aka "hacked space". May as well be using AOL or Yahoo! Talk about insecure email servers deeply breached from the inside out!
*IMAP email on top of that! Easily bypass MFA with any of the wide plethora of tools on the market out there!

So I propose M365BizPrem as usual..explaining Defender, Entra ID P1, optional P2, Defender for Business Endpoint Security, Conditional Access policies, built in email encryption, etc etc.

*Nope...he already studied all the licenses, just wants Business Basic. He already purchased Office...because...he needs the "thick desktop app" for their HawkSoft insurance software. He insists that 365 online Office won't work. I try explaining the difference 'tween "365 online"...and ..that it IS the local thick desktop Office app in higher licenses". But he won't believe me. //rolls eyes

*Where did he purchase the Office app licenses? From some cheap online place. Several of them failed to activate, and he calls them to get newly regenerated keys. //rolls eyes again

*Oh...Office 2019. ///rolls eyes yet again

*At least I did talk him into getting Defender for 365 for each user, so at least there was inbound protection against spam/phish/malware.

*I used the built in Microsoft migration tool, works quite well.
 
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But then...I see how he won't even end up being much of a good client.

I have a handful of clients like that, unfortunately. Started out as what seemed like a great referral, then....it becomes obvious why they are moving. I end up putting up with their nonsense because they....mostly do what I suggest. Mostly. Ugh.
 
The IMAP account for the traveling guy was a God sent gift to you...


Settings -> Org Settings

See the search box at the top? Search "Migration"

There's a Yahoo and other webmail accounts option, feed it the guy's email login details and it'll suck in all the mail... folders... everything... no need to even touch his traveling endpoint.

It's the PST guys that kicked your arse. Which is honestly, the thing that's going to continue. Orgs that haven't gotten into Gmail or Exchange at this point are seriously behind, and they will hemorrhage cash to get things done preciously because the process is by necessity completely manual. No amount of Migrationwiz would save you.

New Outlook isn't trying to hurt you, the data is by nature not portable because the local cache is just that, everything is online somewhere. There is nothing local to backup or restore! The silly thing didn't even support local caching until this past December or so!

P.S. All mail migration projects require DNS control, we won't even start without it. If this situation crops up, we get with the customer to transfer DNS control to Godaddy, Cloudflare... anyone they can own. The tiny web site guys are the absolute worst! As are the "marketting" companies that pull this junk. It's part of my standard discovery when these ops come up, and yeah... it's terrifyingly common even with larger orgs!
 
Settings -> Org Settings

See the search box at the top? Search "Migration"

There's a Yahoo and other webmail accounts option, feed it the guy's email login details and it'll suck in all the mail... folders... everything... no need to even touch his traveling endpoint.

I don't believe this is true. I can't say for certain since I didn't use the migration wizard, but I do know that neither the calendar data nor the subfolders he had created were visible at all in the web login. When you use the Migration wizard, it pulls the data from the IMAP SERVER, not the local computer.

I believe that means when you have a non-Microsoft IMAP account, New Outlook stores those things (created calendars and subfolders) locally somehow, and apparently there is no way to get that data. You cannot export it, and you cannot copy a file somewhere to import it into "real" Outlook. Not that I could find, anyway.
 
Yeah, usually (probably always)..IMAP holds email only. Calendars and contacts and notes....are local computer only (stored in local Outlook). Or if a rare oddball server...in some proprietary fashion that still requires manual export, and spending many overnights trying to groom a CSV file to import gracefully into Exchange.

DNS...always..always line this up way ahead of time. Ensure you have access to it. And a week before planned migration time, I dial down the TTL on relevant records to 15 minutes......MX, autodiscover, SPF....that I'll be modifying/changing. Help things move quicker on cutover night. And I'll create the OTHER 365 records early on too...they won't disrupt current mail flow..and it's one less thing to do on cutover night.
 
Well, New Outlook syncs email, calendar, and contacts (AKA People) for Gmail accounts flawlessly. That was one of the major improvements in New Outlook compared to Outlook Classic. There's no longer a need for a third party calendar and contacts sync utility and everything's on the Google server and any other clients that sync all three see precisely what you see in New Outlook, including anything you add to contacts or calendar there.

I just created a new appointment in one of my Google calendars to test, and before I could even bring up the web calendar it had synced from New Outlook to Google.

I don't know that this is the case for all IMAP, and probably isn't, but I seem to recall this is the behavior for Google and Yahoo, at least, possibly more.

Addendum: While not 100% accurate (as there is 2-way syncing of contacts, at least for Gmail, but Outlook does "screw up" and result in additional addresses rather than edits to an existing address occurring sometimes) this Perplexity.ai search indicates 2-way sync for mail, calendar, and contacts extends to other than Gmail: https://www.perplexity.ai/search/for-what-email-services-does-n-Y7v11AbmRjS2Xr116Oj7Hg
 
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I don't believe this is true. I can't say for certain since I didn't use the migration wizard, but I do know that neither the calendar data nor the subfolders he had created were visible at all in the web login. When you use the Migration wizard, it pulls the data from the IMAP SERVER, not the local computer.

I believe that means when you have a non-Microsoft IMAP account, New Outlook stores those things (created calendars and subfolders) locally somehow, and apparently there is no way to get that data. You cannot export it, and you cannot copy a file somewhere to import it into "real" Outlook. Not that I could find, anyway.
I'm sorry but yes that is accurate.

IMAP is EMAIL ONLY, it's one of the limitations of the protocol, this has little to do with New Outlook. There are mail clients that sort of work around this by making calendar items into emails in a special folder, but that's an extremely proprietary approach! POP3 and IMAP are both mail only protocols in terms of standards.

As for the rest, PST file support is on the official roadmap, but obviously isn't here today. And is a current very real complaint against the product.

I still stand by my claim that neither version of Outlook should be used as anything but an Exchange client. But the world does what it does, and in this case... that's not great because you're right, until MS gets us PST support you're sunk on the standard import / export play.
 
New Outlook will be used by all my clients (home especially, icloud, cable emails, yahoo, AOL, netsol, hostgator, etc) that want it lol. I have some struggles getting setup, so I tell folks to wait until it's more developed. Esp the home users with iCloud accounts who use the same email for icloud and their let's say earthlink, comcast (most common). But that's when I ask them to setup a business or outlook.com account so we can get it setup right with calendar and contacts.

I'm going to look into this a bit myself, the local stuff in New Outlook, see what I can sniff out.
 
I think if you change the licenses to Microsoft 355 Business standard it would have the exchange and I do believe that would sync the calendars.
If your using Sherweb they also have a program called Drop suite and if I remember its $4.00 to the MSP a month per license to backup everything as a disaster recovery.

With their current setup are they sharing the license on each computer?
 
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