Email: Proton Part 2

Series: Big Tech Alternatives

tl;dr: A few more thoughts about Proton after 2 weeks, including a calendar sharing mess, folders and labels, and mobile sync issues.

I've now been using Proton for a couple of weeks including some time starting to organize all my old data, and wanted to share a few extra notes to follow up on that original post I made right after migrating.

The Calendar Mess

To recap, I have:

1. One calendar for my individual usage now in Proton.
2. One calendar for shared usage in a consumer Outlook. Moving that into Proton is not an option, at least not yet, since I'm not the only one relying on it.
3. One calendar for work usage in a Microsoft 365. Moving this into Proton is definitely not an option as I have no say in organizational IT decisions.

I decided to proceed with sharing calendars between them, rather than having each system in their own app silos. The goal was to see all three visible in:

1. Desktop Outlook and whatever app I'm using on mobile for the Outlook account.
2. Proton Calendar on both desktop and mobile.
3. Google Calendar on mobile, for a nicer widget and to be able to see them on my Pixel Watch. (This is not directly the same issue, but is another nuisance for me. The Google Calendar app on my phone will show calendars from other apps that support device syncing, but if I want them on the watch, I have to share them through the cloud to Google.)

I know I won't be able to edit them all from the other sources. That's fine. I can handle opening a different app for changes. I just didn't want to have to consult three apps each time I tried to determine whether I was free at a given time.

This seemingly simple goal has taken me down an absolute rabbit hole of nuisances.

Timezones Suck

First, I immediately encountered an issue that is a combination fault of the trouble with sharing calendars across ecosystems and maybe a little bit extra blame to Outlook. I don't think this is really Proton's fault.

The issue came down to one of the things I hate most as a developer: time zones (and daylight saving time). In short, Outlook does not specify a default timezone at the calendar level when shared. Many apps will specify the timezone at the level of each event, including desktop and web Outlook. Unfortunately, the app I was using on Android called Nine did not do this.

Once I shared that Outlook calendar to Google, Google treated it like those events were in UTC time, showing them but at the wrong time. When I shared it to Proton, those events didn't show up at all because it didn't know what time to treat them as. Other events, the ones created from desktop Outlook, were fine. It was very confusing to look at different apps and sometimes see an event in the right time, sometimes in the wrong time, and sometimes not at all.

I found and changed a setting in Nine. That theoretically solved creating future events with a timezone on them. As far as Google is concerned, it seems to have fixed the display issues, with the events now showing up there properly. It doesn't seem to have fixed it for Proton, though, where those events still don't show up at all. That means I would definitely find myself looking in Proton Calendar occasionally - even if that's not my primary choice for viewing all the calendars, I need it for editing my individual one - and not realize that I'm missing an event from the shared calendar. So that part is only half fixed. I'll come back to the next half in the other section.

Before that, though, I needed to find some way to fix all the existing events, and Gemini helped me by offering a VBA script that I could run in desktop Outlook to find all events without a timezone and to apply mine to it. It feels silly that this was even necessary, but it was.

Seriously, can we just ban time zones and DST and have everyone use UTC and avoid all this?

Task Management

So if there is simply no way to add events in Nine that would be readable from Proton, what is my next option? I could stop using Nine, using the Outlook app instead. Outlook mobile is fine for its email and calendar, although I definitely do prefer to use the independent app when given the choice and I actually have really come to like the Nine interface that is both powerful and easy to use.

Here's my next problem, though: task management. Previously, I was using the built-in task management of Outlook accounts, seeing them easily on Outlook desktop and in Nine, with tasks split between the personal and the shared account.

The Outlook mobile can view tasks within it, but without a dedicated widget, so I either need to keep Nine just for that or also use the Microsoft To Do app. Microsoft To Do is mostly fine except for their baffling decision to not allow showing tasks from multiple accounts in the same view, but that's another app I need.

What does make it a little easier is that the other party in the shared account did not really use the task management there the way they did the mail and calendar, so I do have a little more freedom to stop putting data there at all. So I decided to move all the tasks into one account instead of split between the two. Proton doesn't have task management at all, which to me is its largest glaring hole in functionality, or that would be the obvious choice. Failing that, I could use Microsoft To Do, but with all the tasks moved into one account. I also tried out Google Tasks and quickly didn't like it as much. Maybe there's some third party but in my early searches I did not find much that is both free and as useful as Microsoft To Do.

So ultimately, I ended up with another case of my efforts to rely less on US Big Tech resulting in getting a lot of the most important data out, but actually needing more apps including more controlled by those Big Tech companies. I named this in my introduction post to this series, that perhaps the biggest advantage of those Big Tech ecosystems is how you can do everything in one account, and I really started to feel it with this move. It's worth it, but it's a real loss.

On mobile, instead of just using Nine (an independent app) for 2 Microsoft accounts of email, calendar, and tasks, I now need to use:

• Proton Mail (for my mail)
• Proton Calendar (for my individual calendar)
• Outlook (for the shared email and calendar)
• Microsoft To Do (for both my individual tasks and shared tasks)

Plus Google Calendar but that's less about this migration as about the Pixel Watch thing.

Desktop is better, only splitting from one app into two, Outlook Desktop and Proton Desktop.

This is annoying. It's not unworkable. But it's definitely annoying.

Folders and Labels

In Outlook, I almost exclusively used folders for organizing. It does have support for category tags, but it always felt weirdly tacked on so I never really made them part of my workflow. Folders have one advantage, that they can be nested under each other for greater structure. Folders do have some big downsides compared to labels, though, in that an email can only be in one folder at a time, and you can only view one folder at a time. Labels allow multiple tags on the same email, are easy to set up rules to automatically label by sender or subject, and you can view everything in one place with the labels showing as a quick way to identify what you're looking at.

Proton offers both, with roughly equal importance in the interface. Arguably the folders gets a little more priority, as they are shown first in the sidebar for both desktop and mobile, but both are made easy enough to use.

That led to me re-evaluating how I want to organize my data, with less folders and more labels.

Version 1

I started with a bit more folder-heavy approach with a guideline like: use folders for specific discrete projects. These are the time-limited things with clear edges to them. This allows me to see those specific projects quickly, and when I'm done, move the entire folder into an "Old" section and out of the way but still easy to find if I want it.

Labels in this scheme then would be more dynamic and general ideas, like "Expense" or "Web Development" which may span multiple projects or general ongoing life. Messages may have a label and be in one of the folders, or may go to the general Archive.

There are two minor nuisances to this approach, though:

• Proton includes a default Archive folder for all archived messages, and I can't archive one of my folders while maintaining the folder itself, so I need to have a different "Old" folder to hide it under instead if I still want to maintain the sense that all of these things go together as one discrete project.
• It also doesn't hide on mobile where the folder levels can't be collapsed. They're all going to take up space in the sidebar. That means I have this long list of folders I have to scroll past first in order to get to labels, which is what I now want to rely on more heavily. It's fine on desktop, where the folder can collapse, but does feel backward and like there's no advantage at all to folders on mobile.

Version 2

After trying that for a bit, what I've found is essentially: on mobile I wish everything was a label, because folders don't collapse anyway so I may as well have some flexibility and seeing them for quick identification in the inbox. I suspect, or at least hope, that eventually those folders will be able to collapse on mobile as well, but they can't yet.

On desktop I wish the old archives were folders, since I can collapse those out of the way, while ongoing things get labels which are more flexible but harder to get out of the way.

In that case, assuming that mobile will eventually have collapsing folders, my new goal makes sense to be: label everything current and use folders for some old discrete past categories. There may be points for a lot of things where I convert a label into a folder when it becomes time to archive it.

I think I'm moving in the right direction. It may not quite be fully there yet. But I think this is at least better than being all folders all the time like I did in Outlook.

Mobile App Folder Syncing

Related to the folder and label decisions, I had some issues with mobile app syncing. I was getting new messages. I could compose new or reply and they would send properly. But if I added a folder on desktop or web or even on the mobile app itself, that folder would not appear. It wasn't a matter of time either; I waited for a couple of days with no change showing. Similarly, if I moved an email into a folder (including deleting or archiving it) from web or desktop, it continued to just sit there in my Inbox on mobile.

I opened a bug report from the handy tool in the mobile app. I didn't hear back in over 24 hours. I then uninstalled the app and reinstalled it. The issue went away and everything seems to sync again, not happening again since. I reported that back on the bug report, and had a reply the next morning. Maybe it was a broken cache issue because of the mass import of so much data? That's not ideal, but if it isn't a widespread issue I would get why it's not the highest on their priority list. In terms of the customer support, over 24 hours to reply isn't great either, but it also was far from an urgent issue so maybe they did some triaging and concluded that they could afford to let me wait a bit longer. I'm not going to put too much weight on that as my first experience with their customer service.

Quick Unsubscribe

Let's end on a positive note, because I feel like this post sounds too negative so far about a change that I am ultimately very happy that I have made.

One more feature I quickly discovered and I want to highlight is the quick button to unsubscribe from newsletters. Most newsletters have that link somewhere - at least in Canada they legally have to - but Proton helps make it easy to spot by adding a big button to the top and then it takes care of it from there. I don't need to find the link, enter my email again even though I just followed a link from my email, fill out a form about why I want to leave, click submit, then get one more email begging me to come back. This ease of use Proton offers really makes unsubscribing much more trivial and now I will always do it when I think I should unsubscribe, instead of giving up and deleting it in perpetuity instead.

It may not always work perfectly. I've used it a few times and not heard anything from that sender again, suggesting it completely worked. There was one that I was still getting emails from the next day after I had tried Proton's unsubscribe button, so I used the link instead, and haven't heard from them since. There are also some with more complicated setups with multiple options for the newsletter, not a simple unsubscribe button, and it does not even try to handle those. In other words, maybe this quick unsubscribe isn't perfect, but the ease of use makes it still worth always trying first.

There's also a dedicated Newsletters view that makes it easy to review all of the bulk mail I've received and quickly unsubscribe if I need to do a purge, which is nice.

Conclusion

Overall, I'm still very happy with the change overall. Everything that made me want to change is still true: relying less on a Big Tech company and in turn helping support a company that would benefit from it, better security, more confidence in maintaining my custom domain that Microsoft doesn't offer anymore, and some clean UI including the better use of labels. I may get annoyed at some of these little hiccups that come with supporting a smaller company, but I still think it's completely worth it and I don't intend to change back.