GMail Migration

denverpilot

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Well not much news on the aviation front, I've been doing real work at the office for the last couple of weeks.

Been evaluating moving the six companies in the building from our own hosted Zimbra server to GSuite/GMail.

General thoughts so far:

AD/User Management:

Active Directory integration for users/groups/distro lists/contacts, all seems to work well. We should be able to continue to manage the entire user base from a single location, which is nice. Side effect: Could even point some of the cloud services we use at Google's OAuth engine after this, instead of managing the users and permissions on those separately.

AD Password Sync: Flawless. Big deal and not a single problem no matter how much we beat on it.

Mail Migration:

Initial migration of old mail is a bit of a pain. The devil is in the details. IMAP migration can't be used against a Zimbra server because it doesn't respond correctly with the message's original delivery date/timestamp, so all migrated mail looks like it "arrived" the day of the migration.

Outlook and/or PST file migration gets that part right but dumps the mail headers which removes data that things like GMail's Jira integration use to know the message can be linked to a ticket system to display the stuff like the "Go to Ticket" button.

Obviously the latter is less of a problem than the former, but admin migration of the mailboxes ahead of time was going to be done via IMAP and that's out... can't have the delivery date of 10,000 emails be "today". Ha.

Folders vs Tags:

The whole folder vs tags thing creates some weirdness and need to hand hold each person through straightening out their tags if they're going to stay using a "legacy" mail client like Outlook or Apple Mail.App, etc.

IMAP Migration did this the cleanest of course. Bunch of top level tags of un-nested tags like "Inbox/Customer Issues" or stuff like that but workable for the legacy clients. Outlook / PST Migration makes more of a mess but they're all still there.

Mobile Devices:

iOS has some interesting limitations when attached natively to Google accounts. Biggest one is "Send As" functionally is busted. Can be tricked by adding up to two additional IMAP profiles to the same GSuite account but that's kinda dumb. Android, no problems at all... and...

That's the way around them on iOS : Use the GMail App. Then you're essentially seeing what an Android user sees. (Actually you'd probably use the native stuff for your "primary" address and keep the App around for times when you need to reply as the other address.)

Everything else:

In general it "just works". Haven't really run into any major problems. Calendar imported right. Other stuff. Some Outlook features aren't supported like Categories but I suspect nobody will notice.

Anyone been through this "fun" with a large organization (or six!) and seen any other Bad Things(TM)?

Overall it looks like we are probably still a "go" for this. We're in late eval and other than the highly annoying IMAP Migration issue from Zimbra, it's not looking too bad. The benefits once moved are WAY higher than the problems seen thus far.
 
My previous employer made the transition to Gmail during my time there. I do not work in IT operations, so I can't speak from that perspective, but the migration wasn't a disaster. It appears that Google has enough tools and support in place to make these transitions work fairly well.

The biggest problem that I experienced as an end user was that the Outlook connector (Sync on the desktop) was weak. It worked fine for mail, but calendar sync was frequently broken. In particular, forwarded invites and certain invites from outside mail systems (Lotus Notes was one) became mangled and either wouldn't show up, or wouldn't sync properly. I am pretty convinced that these were Google problems because they would also occur when manipulating invites directly from the web interface.

Frequently, even "normal" invites created in Outlook would sync to the cloud but not to the mobile device (iOS), or vice versa. Google's solution was to remove and recreate the profile, or remove and reinstall Google Sync, but in neither case did that permanently eradicate the problem. Using the web interface rather than Outlook for calendars seemed to resolve the mobile sync issue for the most part.


JKG
 
No comment. :rolleyes:

Rich

I don't like Google either, but their cloud stuff does work pretty well, and their business apps (technically not Gmail as I referenced above) aren't subject to the same snooping as the "free" services (just trust them).


JKG
 
I don't like Google either, but their cloud stuff does work pretty well, and their business apps (technically not Gmail as I referenced above) aren't subject to the same snooping as the "free" services (just trust them).


JKG

I don't know if we share the same depth of hatred, lol.

Rich
 
My previous employer made the transition to Gmail during my time there. I do not work in IT operations, so I can't speak from that perspective, but the migration wasn't a disaster. It appears that Google has enough tools and support in place to make these transitions work fairly well.

The biggest problem that I experienced as an end user was that the Outlook connector (Sync on the desktop) was weak. It worked fine for mail, but calendar sync was frequently broken. In particular, forwarded invites and certain invites from outside mail systems (Lotus Notes was one) became mangled and either wouldn't show up, or wouldn't sync properly. I am pretty convinced that these were Google problems because they would also occur when manipulating invites directly from the web interface.

Frequently, even "normal" invites created in Outlook would sync to the cloud but not to the mobile device (iOS), or vice versa. Google's solution was to remove and recreate the profile, or remove and reinstall Google Sync, but in neither case did that permanently eradicate the problem. Using the web interface rather than Outlook for calendars seemed to resolve the mobile sync issue for the most part.


JKG

Thanks. Passed on to the decision makers. I think we'll live with it if the calendar is a little screwy. Frankly all calendars are a little screwy as soon as you have a mixed device environment anyway, so it'll probably just change who specifically is complaining but not the volume of complaints. :)

No comment. :rolleyes:

Rich

LOL. I knew that was your answer. :)

It was this or hosted Exchange... and none of us could stomach doing that again.

We looked at O365 but their model is even more "trust me" than Google's.

Amazon's isn't even close to being a real offering (not even sure why they're bothering... way outside their swim lane).

We even tossed about the idea of using some really good folks who know mail and mail systems scary-well... near you, Rich... fastmail.fm.

There's a few folk there who can recite the RFPs for every protocol from memory and then tell you which ones everyone is breaking and why. Worked with a couple of them on some problems back in the day, and they're freaky-smart on email backends there.

I've been migrated over for half a week and it's already a better experience than our own Zimbra box. The last sysadmin was the controlling type (well aren't we all... he was off the scale) and wouldn't do Exchange even when they were an all Windows shop... but strangely liked Zimbra. It's okay. But it has warts. As anything trying to mimic an Exchange server naturally would, that isn't an Exchange server.

Gotta admit... I don't think there's a better spam filtering engine on the planet than Google's. Just watching my own stuff after transition, it's just so close to perfect it's awesome. Just getting out of the anti-spam never ending Cold War will be a huge bonus in time and job sat for the admins overall.

Users who have ten year old or more unchangeable email addresses, will probably be shocked at how quiet their noise floor gets. And if anything gets through they mark it spam and the engine gets even smarter.
 
Thanks. Passed on to the decision makers. I think we'll live with it if the calendar is a little screwy. Frankly all calendars are a little screwy as soon as you have a mixed device environment anyway, so it'll probably just change who specifically is complaining but not the volume of complaints. :)



LOL. I knew that was your answer. :)

It was this or hosted Exchange... and none of us could stomach doing that again.

We looked at O365 but their model is even more "trust me" than Google's.

Amazon's isn't even close to being a real offering (not even sure why they're bothering... way outside their swim lane).

We even tossed about the idea of using some really good folks who know mail and mail systems scary-well... near you, Rich... fastmail.fm.

There's a few folk there who can recite the RFPs for every protocol from memory and then tell you which ones everyone is breaking and why. Worked with a couple of them on some problems back in the day, and they're freaky-smart on email backends there.

I've been migrated over for half a week and it's already a better experience than our own Zimbra box. The last sysadmin was the controlling type (well aren't we all... he was off the scale) and wouldn't do Exchange even when they were an all Windows shop... but strangely liked Zimbra. It's okay. But it has warts. As anything trying to mimic an Exchange server naturally would, that isn't an Exchange server.

Gotta admit... I don't think there's a better spam filtering engine on the planet than Google's. Just watching my own stuff after transition, it's just so close to perfect it's awesome. Just getting out of the anti-spam never ending Cold War will be a huge bonus in time and job sat for the admins overall.

Users who have ten year old or more unchangeable email addresses, will probably be shocked at how quiet their noise floor gets. And if anything gets through they mark it spam and the engine gets even smarter.

I can't think of anything bad to say about fastmail.fm. They're probably the best mail provider I've used. Netaddress isn't bad, either, although their uptime could be (and used to be) better.

As an aside, on the mail servers that I run myself using Exim and Dovecot with SpamAssassin, SpamCop, and SpamHaus, the spam filtering has been extraordinarily effective lately. I find myself checking the logs for false positives because I can't believe how little spam is getting through.

As for Google, I had one client switch his mail over to them a couple of years ago. He was a Millennial who was taking over his dad's business and was a real Google fanboy. I was just as happy, actually, because the company had huge mail needs both in terms of volume and size of messages. (They were a plumbing supply company that sent and received bazillions of blueprints and .dwg files.)

I retained the Web site for a while until I non-renewed him and told him to find someone else. The main reason I fired him was that he wasn't happy with Google's mail services, but he kept directing his complaints to me, even after I repeatedly told him that I couldn't do anything about them because I no longer was his mail provider. It got annoying enough after a few months that I finally non-renewed the whiny little putz after an almost 15-year happy business relationship with his dad.

His biggest complaints were slow delivery of incoming mail, and his outgoing mail being bounced because whichever server Google happened to relay it through was on someone's RBL at that particular moment in time. Apparently back then they used the same servers to relay his mail as they did to relay gmail. I don't know if that's still the case, but if it is, then random false-positives on outgoing mail because the relaying server is on an RBL is likely to be your biggest problem.

Rich
 
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His biggest complaints were slow delivery of incoming mail, and his outgoing mail being bounced because whichever server Google happened to relay it through was on someone's RBL at that particular moment in time.

Ah, yes, that jogged my memory. My company did have occasional instances of slow delivery of incoming mail--often several hours delayed. The worst part was that you didn't know until someone called you in reference to an email that they sent a few hours ago, or you saw a new reply from someone else to an original email which you hadn't yet received but would eventually come through hours later. This tended to be a widespread problem when it occurred. I'd estimate that we had this problem maybe once a quarter, and it was usually cleared up within 24 hours. There were some cases of coworkers complaining that their outgoing emails didn't go through to customers, but those seemed to be fairly isolated.

The other big frustration with Google as an end user was that locating documentation (especially for Known Bugs) was painfully difficult. It could be done, but for a company who specializes in search, it sure seemed like they made it intentionally difficult to uncover documented problems with their products. If I were considering migrating to Google, I'd want to review a list of Known Bugs with the service, the connectors, and their ActiveSync capability across multiple devices just to make sure there aren't any landmines which might impact my company.

Honestly, MS probably does all of this better than Google, but I've heard from some folks who don't like O365 for other reasons. My new company runs its own Exchange environment, and it isn't problem-free, either. I agree with Nate, in a mixed-device environment it's probably tough to get it perfect, but for a larger-scale e-mail/calendar/contact platform I think that Google does a decent job (even though I strongly dislike them). But again, I've never seen things from the IT operations side of the table.


JKG
 
Ah, yes, that jogged my memory. My company did have occasional instances of slow delivery of incoming mail--often several hours delayed. The worst part was that you didn't know until someone called you in reference to an email that they sent a few hours ago, or you saw a new reply from someone else to an original email which you hadn't yet received but would eventually come through hours later. This tended to be a widespread problem when it occurred. I'd estimate that we had this problem maybe once a quarter, and it was usually cleared up within 24 hours. There were some cases of coworkers complaining that their outgoing emails didn't go through to customers, but those seemed to be fairly isolated.

It still happens with gmail, but I don't know whether it happens on Google's paid mail service. I still occasionally get complaints from clients whose mail from gmail users was bounced back. When I troubleshoot it, it's invariably because the relaying server was blacklisted by either SpamCop or SpamHaus.

My response is always something along the lines of that being part of the cost of freemail. More than 90 percent of my actual incoming spam is from gmail, hotmail, or outlook addresses, and once in a while legit users pay the price for all that spam. It's like living in a neighborhood full of hoodlums. When you live with hoodlums, you're treated like one, too.

On the positive side, usually all the sender has to do is re-send the message, and it will go through. Gmail is relayed through so many servers that it's unlikely to go through the same one twice in a row. If the sender is an important contact for a client, I'll whitelist the address for them (or tell them how to do it themselves if they're a hosting-only client).

Rich
 
Yeah, G has it's issues and I really don't trust them. Same with MS.

I've looked at Amazon for a small company and it's pretty apparent that they're not really serious about it. Outlook 2016 on Mac won't work with Amazon (though Outlook 2016 on PC will), and no pop/imap support.

Rackspace has both hosted exchange and their own solution. Not sure about the support. On the hosted exchange front, AppRiver seems to work pretty well and as best I can tell has great support and a very good anti-spam engine. Then you get into full SMB solutions like Intermedia and Zoho.

Given experience, I'm probably going to be moving one small business that only needs email to AppRiver. Getting to be a pretty big pain to run server in-house these days.
 
Yeah, G has it's issues and I really don't trust them. Same with MS.

I've looked at Amazon for a small company and it's pretty apparent that they're not really serious about it. Outlook 2016 on Mac won't work with Amazon (though Outlook 2016 on PC will), and no pop/imap support.

Rackspace has both hosted exchange and their own solution. Not sure about the support. On the hosted exchange front, AppRiver seems to work pretty well and as best I can tell has great support and a very good anti-spam engine. Then you get into full SMB solutions like Intermedia and Zoho.

Given experience, I'm probably going to be moving one small business that only needs email to AppRiver. Getting to be a pretty big pain to run server in-house these days.

I'd take a look at Fastmail.

Rich
 
Part of the problem these days is that for enterprise level email services (i.e., supporting more than 20,000 employees), your only realistic options are Exchange (hosted or onsite), Office 360, or Gmail. There are tons of better providers and they have lots of features that make them worthwhile, but trying to make them work for 10s of thousands of employees is not realistic.
 
We ran into weirdness with ALL methods of import of old mail. (So tempted to create a "green field" new system and tell folks they'll have access to their old email for month on the old system and then shoot it in the head to put it out of our collective misery, but alas...)

Crazy thing is: Out of all the ways one can move mail, calendar, and contacts from the existing system to Google, the freaking Google plugin for OUTLOOK handles the import the best.

Server to server? Broken. Google refuses to parse dates out of the headers and if the mail server it's suckling from doesn't implement certain aspects of the IMAP FETCH protocol, they just give up.

PST... now THERE was some fun. Well two stages really. We purchased a tool that comes highly recommended to covert from Zimbra's native export format to PST so it can be gobbled up by Google. No es bueno. Makes a mess.

So we're in a hold in the countdown but may have to suck one account at a time into Outlook and then import. There's a way to do it with PSTs but it's horribly manual and ugly.

We have users who say they don't care and want to go "right now" so I guess that shows how bad they want it. Some of them anyway.
 
We ran into weirdness with ALL methods of import of old mail. (So tempted to create a "green field" new system and tell folks they'll have access to their old email for month on the old system and then shoot it in the head to put it out of our collective misery, but alas...)

Crazy thing is: Out of all the ways one can move mail, calendar, and contacts from the existing system to Google, the freaking Google plugin for OUTLOOK handles the import the best.

Server to server? Broken. Google refuses to parse dates out of the headers and if the mail server it's suckling from doesn't implement certain aspects of the IMAP FETCH protocol, they just give up.

PST... now THERE was some fun. Well two stages really. We purchased a tool that comes highly recommended to covert from Zimbra's native export format to PST so it can be gobbled up by Google. No es bueno. Makes a mess.

So we're in a hold in the countdown but may have to suck one account at a time into Outlook and then import. There's a way to do it with PSTs but it's horribly manual and ugly.

We have users who say they don't care and want to go "right now" so I guess that shows how bad they want it. Some of them anyway.

Other than fanboys who simply love Google, if the system delivers the mail, why do people hate it so much? Mail is mail as far as I'm concerned, as long as it works all the time. That's really all I care about in the end.

The client I fired after they switched to Google as their mail provider, in addition to being a fanboy, simply hated local mail clients in general. He hated "all of them," he said, and "couldn't understand" why he should have to use a mail client to check his mail.

I thought that made as much sense as not being to "understand" why he needed to use a Web browser to browse the Web, a file browser to browse files, a bookkeeping program to keep books, or an instant messaging client to send instant messages. Mail clients are designed to access mail. That's why he has to use one. It seemed pretty clear to me. But some people are funny that way.

He also didn't like any of the three (at that time) webmail clients that I offered (SquirrelMail, Horde, or RoundCube) that were bundled with his cPanel hosting (which he also didn't like, but insisted on anyway because he liked Plesk even less); but he also refused my offer to install literally any Linux webmail client in the world for him, at whatever my cost would be for the license, and without any charge for my time installing it. His dad had been my client for many years and I had known most of his users (and him, as well) since he still thought girls had cooties, so I was willing to bend over backwards for him.

In the end, however, it was pretty obvious that he liked Google's webmail interface, and only Google's. Which I guess is fine. Personally I think it's slow and clunky, but so are Webmail interfaces in general. I really can't say that Google's sucks any worse than the rest of them in that regard. But really, how much difference is there in Webmail apps? RoundCube is probably the best and most stable of them, in my opinion and experience; but they all offer the same basic functionality.

Netaddress (usa.net) used what looked suspiciously like re-branded Horde to me for many years. It was perhaps the ugliest webmail client I'd ever used. But I didn't care. When I was away from my computer and mail client and needed to use the mail, it was as usable as the rest. I mean, it's webmail. Once you get past the appearance, webmail is webmail.

I've also had clients switch over from Outlook to Thunderbird (or vice-versa), and their users either celebrated or whined about it for months. Again, I don't get it. I happen to like Thunderbird because I don't need Outlook's functionality and Thunderbird is faster. The Lightning plugin also interfaces nicely with my Fastmail calendar, which in turn works nicely on any mobile phone I've ever used since I've been using Fastmail. So Thunderbird with the Lightning plugin works for me. But if I had to use Outlook (or Opera mail, or Windows Mail, or anyone's webmail), I'd shrug and use it. Mail is mail. As long as it works, I'm pretty happy.

My favorite email client of all time was Qualcomm's Eudora Pro. But alas, it's gone, unsupported, and doesn't play nicely with recent Windows versions, even in compatibility mode. RIP.

As an administrator, the only mail client I hate is Apple's. That's because literally 100 percent of my support tickets for mail clients that suddenly stopped collecting and sending mail for the past seven years or so have been from iThing users. And they all happen at the same times. I'll get dozens of tickets from iThing users on the same day, and then none for months. I suspect undocumented silent updates are the cause because I can't think of any other good reason why so many iThing users should have mail problems on the same days. But I digress.

What I suspect is that many of your mail users simply like Google's GUI because that's what they're used to. I don't think it's anything special, but some people think it's the epitome of mail interfaces. Also, I suspect that many users nowadays are just lazy. They're used to things being a certain way and functions being in certain positions on their screens, and they're unwilling to invest literally the two seconds that it takes to scan the screen to find the most common mail functions. They get all whiny and start throwing tantrums.

As an aside, after my aforementioned whiny client made the switch, more than half of his users refused to use the Google interface. They kept using Thunderbird, which had been the company's standardized mail client pretty much since the day it was introduced. Eventually he disabled POP and IMAP access to force the users to use the webmail interface.

Why was he so insistent that they use webmail? No idea. To me it seems like he just had control issues. I can understand standardizing around a desktop mail client for ease of support, but it's not like Thunderbird is high-maintenance. Yeah, the .msf files **** the bed once in a while, but I'd given him a batch filed that deleted them all en masse, which would always fix the problem. Even if he wanted to keep the mail on the server for whatever control-issue purposes he may have had, all he had to do was require that his users use IMAP (which had always been company policy, anyway). But that wasn't enough. He wanted them to use Google's webmail, period.

Again, I shrugged. I really didn't care which mail client he used, especially since I was no longer his mail provider. The fact that he kept me apprised of these things was actually more of an annoyance than anything else because once he moved his mail, all things mail-related became irrelevant to me and a waste of my time. I was actually pretty happy that he moved because he'd been using about 30 GB of my storage space. Once he moved the mail, I was able to free up about 29 of those GB for other use. That savings was the reason I kept listening to his whining for as long as I did.

But after a while, even that wasn't enough compensation, so I non-renewed him. I even helped him find hosting for his Web services and migrated everything over for him at no charge. I just got tired of his incessant, unremitting whining and wanted him gone.

Rich
 
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Did this in a 50 person company, and it worked out very well. Only one or two people had outlook on their desktops after a few months.
in my opinion, it is fantastic for a small business. No more huge IT bills. At the time it was by far the best web portal to email and still darn great. In all honesty, no one wants to check email with a desktop client. If they had to I would install Thunderbird. If they still complained, they went back to outlook. No loss for anyone really.



AG
 
Did this in a 50 person company, and it worked out very well. Only one or two people had outlook on their desktops after a few months.
in my opinion, it is fantastic for a small business. No more huge IT bills. At the time it was by far the best web portal to email and still darn great. In all honesty, no one wants to check email with a desktop client. If they had to I would install Thunderbird. If they still complained, they went back to outlook. No loss for anyone really.



AG

Well, I wouldn't say "no one." I prefer Thunderbird to any webmail client I've ever used (including Google's) and to any desktop client I've ever used except Eudora Pro (RIP). T-Bird is fast, free, intuitive, extraordinarily customizable, versatile by way of extensions, relatively lightweight, and fairly robust. Other than the occasional corrupted .msf file, it's one of the most trouble-free pieces of software around, in my opinion.

Even the occasional .msf corruption that has long been the only real annoyance in T-Bird is getting rarer, and is easily fixed in any case. Compare deleting some .msf files to dealing with a corrupted .pst file in Outlook. There's no comparison. I mean, seriously, an entire cottage industry has sprouted up around recovering corrupted .pst files -- and Outlook is a fairly expensive piece of proprietary software.

So yeah, I like Thunderbird. I even contribute money to them regularly -- and I don't part with my money easily, to which anyone who knows me will attest. I throw nickels around like manhole covers. But as much as I like Thunderbird, it's not something I couldn't live without. In the end, it's just a mail client.

Rich
 
I'll try to explain the vagaries of why many want to switch ...

It's definitely not all about the UIs in use. With six companies in the building it's more becoming about Zimbra's relatively weak support of mobile clients and a desire to get calendaring actually working across all users. (Right now, if you don't "do" Outlook like about 25-30 people don't, the only GOOD way to use calendaring is via Zimbra's web mail interface which is somewhere better than RoundCube and weaker than Google for calendar.)

The one thing that GMail offers is that not *just* mail works natively on various desktops and mobiles but mail, calendaring and contacts work (for the most part) on ALL of them. (The notable exclusion is Outlook for Mac and Mac users either want the web interface or they want native integration, both of which work.)

Us old guys that use mail for mail, don't quite get that the kids have always had it all integrated. :)

So mostly it's more of a "Hey, see how all of this stuff works properly across the completely dissimilar user bases?"

The outlook users can invite someone to a meeting and it'll actually show up on that developer's Mac calendar, their Android phone calendar, the web interface, etc.

Whatever gadgetry they have, generally works... and we do allow lots of BYOD...

Then mix that on our side with single point of administration, integration of user and password data in one place (ironically Active Directory), and the ability to remote manage the mobile devices (kinda... worst case we can wipe, which is really rude on a BYOD device but commonly required that an IT department can do it), while supporting a very mixed user base of clients, both desktop and mobile.

Zimbra can do SOME of that, even most, but it's clunky. And backing it up and maintaining the actual box it runs on is a minor pain.

The "no standard client" thing really drove Google.

O365 can do it also (amazingly) but there were other reasons it got axed.

Last test import was today and now we know what goofiness each import type will do with labels/folders on all of the various UIs.

Have to admit, having the majority of the admin tools as an app on my phone is fairly appealing also (even looking at logs for problems) but those weren't requirements up front.

Basically it's not GMail's web interface they want. It's "multi device support". Even iPhone has some minor problems with GMail, but you can load Google's own iOS Apps to get around the really weird user issues/needs. (Like having more than three "send as" addresses with a single mail account. There are ways to trick iOS into doing that or you just launch the GMail App and switch your "send as"...)

Again a problem not most places will have. Six companies in one building -- the bosses sometimes want that domain suffix to say "company three" instead of the parent.
 
PS I'm an old fan of T-Bird from way back. It even solved a problem today for a boss who wanted to keep an archive of two long fired consultants... export their mail to local disk, give a copy to the bosses, attach it to T-Bird. Done. Easy.
 
I am stuck with Outlook for a variety of reasons ( both for PC and Mac/2016), as well as android and iOS, and a web interface.

What do we like as a Caldav or similar plug-in that will allow Fastmail and some other platforms work with Outlook?
 
I am stuck with Outlook for a variety of reasons ( both for PC and Mac/2016), as well as android and iOS, and a web interface.

What do we like as a Caldav or similar plug-in that will allow Fastmail and some other platforms work with Outlook?

I've read good things about Evo Collaborator. I've never used it, though. They do offer a trial version.

Rich
 
I cannot stand GMail's interface, and it cannot do something really important to me. But I cannot recall what it is.
 
Oh, and if you don't HAVE to do Outlook 2016 for Mac, stay away. I had to use it for a company purpose, and while it works OK with the newer version of Exchange, and just OK with IMAP, it blows at things you can do with other versions of Outlook. Even ESET's anti spam doesn't work with it. Apples built-in Mail ap, which is not perfect, is better than Outlook. Unless you need outlook for some reason.
 
As someone for whom fixing problems that Outlook caused was a considerable percentage of my income, I never could understand how it became and remained so popular. I always considered it a bulky, bloated, slow, clunky, problem-prone piece of software. Frankly, unless required to do so by someone who was paying me to, I wouldn't use it even if it were free.

But then again, I feel the same way about MS-Office in general. When I was still a Microsoft "Partner," I got all their stuff for free for in-house use, and I still didn't use it. I used StarOffice / OpenOffice preferentially even when I had the latest and greatest versions of MS-Office installed. The only times I opened MS-Office were when I was trying to solve a problem someone else was having with it. I almost never actually used it for my own work.

I wasn't some left-wing rebel who hated MS because they were successful. I just thought that their software wasn't very good -- which was something for which I was grateful because I made a lot of money because of it. I mean, I made hundreds of thousands of dollars just resurrecting Windows and removing viruses and other malware from it. I easily could have done nothing but onsite virus removal and made a very nice living from it. Even as a generalist, malware removal was still a healthy chunk of my income.

In other words, I never hated Microsoft. I just thought that most of their software sucked -- for which I was very grateful. How MS-Office in general and Outlook in particular became the de facto standards when there were (and still are) better (and often free) alternatives out there was and still is a mystery to me.

Even on the server end of things, I scratched my head wondering what other than inertia made MS's server systems so popular. I could do all the same things with Linux, more reliably and at a fraction of the cost, if it weren't for inertia. The only reason most of my small- and medium-business clients needed Windows Server was because they ran some sort of proprietary, industry-specific software that needed it -- and quite often, that software itself was overpriced, buggy, bloated, and out-of-date.

I can't tell you how many times I had to keep machines running old versions of Windows (both server and workstation) running for years after they should have been retired because the companies that put out their pricey, industry-specific software hadn't gotten around to updating it to work with newer Windows versions. And mind you, these programs weren't cheap. The licenses cost many thousands of dollars every year.

Most of these programs were nothing but front-ends for databases. They could easily have been written to run on Linux. In fact, when the publishers of some obscure, industry-specific software products went out of business (or in one case died), I sometimes wrote Linux substitutes that worked just as well for the clients -- and I'm not even a programmer.

But that was okay because the software in question weren't really programs. They were basically Web GUIs to database calls pushing and pulling data from databases. That I knew how to do, and I made quite a lot of money doing it when the support for the Windows versions of some obscure software vanished, along with the publishers themselves.

What baffles me most is that inertia still rules. Companies are pinching pennies to the point of downgrading toilet paper quality and charging their employees for coffee, but they still pay through the nose for overpriced software that in many cases isn't even very good, is poorly-supported, and in almost all cases could have been written to run on Linux -- at a fraction of the cost and with better reliability. I just don't get it.

Rich
 
Oh, and if you don't HAVE to do Outlook 2016 for Mac, stay away. I had to use it for a company purpose, and while it works OK with the newer version of Exchange, and just OK with IMAP, it blows at things you can do with other versions of Outlook. Even ESET's anti spam doesn't work with it. Apples built-in Mail ap, which is not perfect, is better than Outlook. Unless you need outlook for some reason.

It truly is bad.

Google warns that it will regularly exceed their IMAP limits for connections and bandwidth compared to other IMAP clients. It's hideously slow too. And you can see why if you have it running on a nice slow network connection.

It batches nothing and uses none of the IMAP consolidation command subset if you sniff it. If you select 200 messages to delete, it does them one at a time slowly in a loop until it has moved them all to the Trash. Then again when you delete the Trash. It doesn't understand IMAP IDLE, either.

It's just a really poor mail client. It's the one client we will refuse to support after the move.

Native Apple to Google integration works 1000x better, there's always the web interface and there's at least three decent OSX based pay-to-play mail programs that also beat it besides T-Bird.

But frankly for most Mac users it'll be "Add Account --> Google --> Enter AD Username with @companyname.com after it --> Enter synced Domain password... done. Mail, Calendar, Notes, all of it, will sync up and work.

For the PeeCee Outlook users it's going to be "Download Outlook Plugin --> Answer a few questions about what to migrate if we haven't migrated you already --> Domain username/pass... wait for sync if doing it then... done."

Pretty much the same with mobile devices or on iOS, load Google Mail App if you like their interface better. (It's already the default on Android for the most part.)

Three "nerdy" beta users are syncing tonight. They're migrated over and working already. We'll give them a few days to explain any weirdnesses we haven't already documented and we've told them about anything that errored during sync (few calendar events for birthdays seem to have not been happy.... interesting....).

Then we start migrating in earnest.
 
It truly is bad.

Google warns that it will regularly exceed their IMAP limits for connections and bandwidth compared to other IMAP clients. It's hideously slow too. And you can see why if you have it running on a nice slow network connection.

It batches nothing and uses none of the IMAP consolidation command subset if you sniff it. If you select 200 messages to delete, it does them one at a time slowly in a loop until it has moved them all to the Trash. Then again when you delete the Trash. It doesn't understand IMAP IDLE, either.

It's just a really poor mail client. It's the one client we will refuse to support after the move.

Yep. And I never would have had it not been for a corporate requirement. Even 2011 was better. There is an issue with sort-select-bulk delete in that if you sort by sender, it will present a list of collapsed threads, even if there is only one post in a thread. So to sort-tag-delete, it requires opening the thread, then selecting the (often single) message, and then going on the the next. If you get any amount of spam and the spam filter is not working well (or in the case of Eset, not able to work), then you're hosed when you go to bulk select/delete.

And that's in addition to the imap problem you mentioned. Last time I tried to download a second account (imap only) with about 1000 unsynced messages, we hit the server connection limit as a result of the issue. Sucks even worse over a VPN.

I get that MS hates Mac, but this product is just plain embarrassing for them. Once I am able to dump that corporate connection, I'll most likely wind up on Mac's internal clients.
 
I get that MS hates Mac, but this product is just plain embarrassing for them. Once I am able to dump that corporate connection, I'll most likely wind up on Mac's internal clients.

I think it has to do with different business units at MSFT and ancient tech inside PC Outlook. The thing is still using what's essentially an embedded access database inside a file in the PST/OST. Under the hood, it's hideous.

It's clear that Outlook for Mac was a greenfield project built from scratch around the time MSFT decided to go back to supporting and offering Office again on the Mac. (Ostensibly to win over Mac users to O365, which I'll admit, is the easiest way to keep "real" Office apps on up to five Macs with a personal O365 account and at $99 a year, isn't awful.)

But it's obviously also young code and there weren't any real old timer mail gurus on that team, if they let it go out the door behaving like it does. They figured they could tweak O365 to play with it via the direct EWS support and half-ass the IMAP stuff for the most part. That's my guess.

And it's really half-assed. But then again, so is PC Outlook under the hood. File size limits and everything in one file? C'mon kids, maildir has been out for decades...

It's actually one of the interesting things Google apparently did in their sync tool. Sync tool looks like it runs an SQLite DB under itself and then manipulates the PST file directly to integrate with LookOut, er Outlook. They limited how big they'll make the PAT to 1GB and then send you a note saying "you can make it bigger, but performance is going to start to suck balls..."

Then they give you the option of 2GB, 4GB, or "unlimited" with the warning that MSFT has an upper size limit on the file and links to MSFT Docs on how to modify the registry to allow massive PST files. And another warning that performance will probably be even worse than sucking balls.

Outlook is a mess. Office clearly got all the developer love during the days of wanting to support Mac again. In fact, there were versions of Mac Outlook with serious bug fixes that were ONLY available via O365 download that you couldn't get through any other channels for a while. Don't know if they ever synced that back up.
 
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