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The joy of upgrades

Topics/tags: Rants, technology

Yesterday, Grinnell upgraded its Exchange server [1] to use two-factor authentication with Duo [2]. Adding 2FA makes sense. Schools [3] are experiencing a huge uptake in phishing, and 2FA is an appropriate response.

I thought I had prepared myself. I’ve been using Duo for remote login since the spring. I checked the list of supported clients. Both iOS mail and macOS mail seemed to be supported. I’m pretty sure that I even called over to ITS to re-verify, especially since my colleagues were getting email messages that their clients were not supported. When Duo Mobile decided that my iPhone was too old [5], I even got one of the key fobs.

Yesterday morning, I went to check my email on my iPhone. I kept getting an Incorrect Password message [6]. It took me a few minutes to remember that yesterday was the rollout day for two-factor authentication [7]. Instead of bothering the folks at ITS, I decided to try dealing with the issue myself. I found that removing my Exchange account and re-adding it solved the problem [8]. Yay me!

While I was doing that, I was still able to read email on my Mac. That is, the standard Macintosh email client seemed to be working fine. Or so I thought. Then came the afternoon. It, too, was now issuing error messages. I considered employing the same approach that I had used on my iPhone. However, I hate deleting my Grinnell Exchange account from my Mac because it usually takes a day or two to rebuild the mailbox. So I called ITS to see if there was an option other than Delete the account and then add the account. There wasn’t. So I deleted the account, and my Mac deleted all the corresponding email from my hard drive [9].

Then I went to add the account back. And, well, I couldn’t. I kept getting authorization failures. So I called ITS back. I learned that on macOS 10.12 (Sierra) does not support the authorization framework that the College wants. Hence, I needed to upgrade to 10.14 (Mojave). Isn’t that wonderful? I’d swear that information wasn’t on the page when I checked it a month or so ago.

I felt somewhat foolish upgrading to Mojave when Catalina is coming out in a few weeks. But I didn’t really have any options [10]. And I tend to be a late adopter, so I would not have been likely to upgrade to Catalina immediately in any case [11].

I’m not sure why, but upgrading was a slow process. Once I downloaded and ran the installer [12], it indicated that installation would take 4.5 hours, most of which seemed to be downloading the rest of the OS. Why so long? It appears that my Internet connection is slow, slow enough that I couldn’t even run an Internet speed test. I assume that the various email issues on campus are using up a surprising amount of bandwidth. At least I could pretend to do other work while it was installing [14].

After an hour of watching the expected time increase, I reset my Internet connection. That made a huge difference. When I restarted the installer [15], the time remaining dropped from five hours to fifteen minutes. My download speed went from unable to contact server to 50 Megabits per second [16]. Things were looking up. And then the damn connection reset itself. When I reconnected, the download speed was back down to 3.2 Mbps. And then the Mojave installer couldn’t even contact the installation server. Have I mentioned how much I hate computers? Anyway, it appears that it’s a common problem. Fortunately, I didn’t need to implement any of the common suggested solutions. I particularly dislike having to reset the PRAM. After trying to start the installation process three times, I was finally able to connect. But when I connected again, I was back to a four-plus-hour download.

Eventually, I gave up and went home. I looked through some of my backup drives and found a Mojave installer. I didn’t expect it to be for the most recent version of Mojave, but it struck me that installing and upgrading would be faster than trying to install over the Interweb. Installing the OS still took about an hour. The updates were 2.61 GB which, on my slow ISP, took a bit over an hour to download. Whee! There were a few points where that time went up, too. But they never went quite as high as 4.5 hours.

I tried to do some other work while waiting for my MacBook to download the upgrade. One of the first things I discovered was that the Xcode command-line tools that I rely on, like git, were no longer installed. I didn’t want to waste the extra bandwidth waiting for them to download, so I had to figure out other tasks to undertake. Bleh.

Once I got everything set up, I added my Grinnell Exchange account. Then I realized that I needed to upgrade my GPG software. That worked reasonably well. It took a bit to find my verification code, which was buried in my email. But when I uploaded my keys to the server and tried to click the verification links in email, verification failed. Since verification worked for my Gmail account, I blame Proofpointless for munging the verification URL.

The experience of adding GPG Tools to my mail client reminded me that (a) I really can’t use Exchange on the Mac, since it doesn’t support PGP and (b) I’ll need to delay the upgrade to Catalina until those tools are updated to support Catalina.

Somewhere in the middle there, my Web pages stopped working correctly. I use UTF-8 for my page encoding. For some reason, our server was reporting that may pages were encoded in ISO-8859. I didn’t think the problem was associated with the email or OS upgrade, but you never know. I spent some time looking around to see if the default encoding was set somewhere in the OS. Eventually, I gave up and dropped a note to our SysAdmin. I got the answer this morning. It appears that another faculty member asked our SysAdmin to set ISO-8859 as the default on Apache and that broke things. The compromise of having no default seems to have worked.

This morning, I was reminded of why I hate the strategy of delete your account and then add it again. Even after a night of updating, my email client says that there are more than 270,000 messages to download.

I was also reminded why I don’t like upgrading my OS. For some reason, Firefox has slowed to a crawl. I suppose it doesn’t help that I have more than a dozen windows open, many with a dozen or more tabs. But it behaved reasonably on macOS 10.12. I suspect that there’s something to do with how memory management works under 10.14. And it does use a lot of memory. Let’s see … Right now, Firefox is using 4.88 GB of RAM, FirefoxCP WebExtensions are using 632 MB, and there are eight FirefoxCP Web Content processes, using 1.73 GB, 914 MB, 885 MB, 785 MB, 634 MB, 586 MB, 528 MB, 484 MB, and 329 MB of RAM. That’s a lot. I guess it’s time to start bookmarking or removing windows. It may also be time to switch my Web browser. But it’s frustrating.

Altogether, I lost about a day and a half of sabbatical time. Nonetheless, I’m glad that I’m on sabbatical. If I’d been in the midst of classes, dealing with lost work time and difficult-to-access email would have been unbearable. I send sympathy to my colleagues and students who were in that situation.

I’m also someone who is (or should be) technically informed. I expect that this was even harder for folks who are less informed. Or perhaps they just passed the problems on to someone else. And most people don’t keep as much email around as I do.

I’d like to be able to blame someone for all of this difficulty but there’s not really anyone to blame. I don’t blame ITS. As I noted, I know that we need two-factor authentication. And I’m not sure that there’s a better time to do an upgrade like this. You need a time in which people are on campus since fixing issues often requires face-to-face contact. The end of the semester is bad; people are racing to finish too many things. The beginning of the semester is equally bad. And they didn’t want to delay too long. So this seems like an appropriate time to roll out DA. And I know that they made sure to have a large cadre of people available to help. I don’t blame myself. I did the things that I was supposed to do in advance. I don’t blame Apple for not having the appropriate Microsoft authentication in macOS 10.12; I’m not sure what state it had. I don’t blame Microsoft for a strange authentication system [17]; their clients clearly wanted something like this. Should ITS have been aware of these likely problems? It would have been nice. But my sense is that the problems were not well documented. The one thing I really would have liked was an easily available self-help page with easy-to-find and up-to-date information. For example, it took some time to remember that the instructions for configuring email accounts on iPhones are in the student setup documentation, and those instructions don’t include the Duo issues.

Are there things that we can take away from all of this? The experience suggests that technology rarely works as easily as you expect. But I’m pretty sure that people knew that already. That you need to explore a wide range of situations? That’s also something I expect people know. But situations are difficult to predict. For example, you might find that you can connect to the Duo-enhanced [7] server with iOS mail, but not realize that it only works if you did not have a prior account set up on that server. That people [19] should run up-to-date software? There are certainly reasons to run older software, from concern about the effects of upgrading [20] to an inability to upgrade because of hardware limitations [21].

Postscript: At times, computers seem to bear a resemblance to old houses. Just like every project in an old house begets new projects, so does every upgrade or change on a computer beget new upgrades.

[1] Or is it an Office 365 server? I can never tell.

[2] And, perhaps, other services.

[3] Not just Grinnell.

[4] That document is behind a password wall.

[5] It’s an iPhone 5S. It’s starting to get old enough that Duo doesn’t quite trust it. That is, Duo reports that I need to upgrade to iOS 13. However, iOS 13 doesn’t run on the iPhone 5S. 12.4.1 is the currently supported version.

[6] That message is paraphrased.

[7] Or maybe it was yesterday.

[8] Further conversations with ITS suggest that (a) I chose the appropriate process and (b) the need to remove/reinstall the account is a known issue, but Apple does not have it clearly documented.

[9] At least I think it did. I suddenly had much more space available on the hard drive.

[10] That’s not quite true. I could use Outlook for Mac. That seems less palatable to me than upgrading my OS. Maybe I should give Outlook a chance. But not today.

[11] Sidecar seems to be an appealing technology, so I may upgrade more quickly than normal.

[12] Or part of the installer.

[14] Writing this musing falls within that model.

[15] It quit when I disconnected from the Internet.

[16] I was using the standard Google Internet speed test.

[17] Well, maybe a bit.

[18] sic.

[19] That is, me.

[20] As in this set of experiences.

[21] As in my iPhone.

Version 1.0 of 2019-10-02.