Why I left Ulysses

Just months after proclaiming my allegiance to the Ulysses writing app, I’ve chosen to abandon it in favor of iA Writer.


Note, 2019-05-04: I’ve learned some additional information since the original post (2019-04-20) which doesn’t truly exonerate Ulysses regarding the sync issues described herein but does raise serious questions about just where the fault really lies. So I went back and renewed the Ulysses sub after all. For details, see “Boxed in.”

I quit using Ulysses today.

I also cancelled my annual subscription to it, which was due to expire in five weeks.

A few months ago, I couldn’t have imagined writing those sentences at all, much less posting them here.

After all, one of my most-viewed posts was my explanation of why I had settled on Ulysses as the daily driver for my writing. The people at Ulysses even linked to it from their monthly e-newsletter, obviously the reason for its being so visited. (Quite understandably, they won’t be linking to this one.)

I wrote for nearly a year within Ulysses, both for this site and in my swear-I’m-gonna-finish-it-while-I-still-remember-how-to-form-sentences work in progress (WIP).

Ulysses was a delight to use on the Mac and my iOS devices. The UI on each seemed perfect for me. Ulysses had just the right mix of features for my creative writing, neither so many that I’d feel overwhelmed nor so few that I’d feel restricted.

I particularly admired how it sync’ed my content, via iCloud, so swiftly and automatically among my Apple devices.

Although I became curious about other writing apps, even if only for creating content for this site, I steadfastly insisted that they would be, at best, only add-ons; they couldn’t begin to replace Ulysses, especially for long-form writing.

So what happened?

It’s complicated. In fact, I’ve been working on this post for several weeks now, as it became clear that this was the direction in which I was heading. I wrote this along the way so that, when the time came and I actually pulled the plug, I’d have all my story-telling ducks in a row for you.

Pull up a chair, metaphorical or otherwise, and I’ll use my new daily writing driver, iA Writer, to tell you all about it.

The blog slog

At the beginning, I wished only to make blogging a little less tedious.

I’ve mentioned from time to time over the last few months that I was experimenting with other Markdown editors. While I still enjoyed writing this site’s posts in Ulysses, I’d wearied of the write-export-write-export dance it required because the native Ulysses file format is proprietary, not the standalone Markdown (.md) needed by my static site generator of choice, Hugo. Thus, I was trying writing apps that saved natively to Markdown without needing to export.1

Screen capture of Quick Export feature of Ulysses app

Ulysses’s Quick Export feature: the only way you can derive a true, standalone, visible Markdown file from one of its native, proprietary-format files.

Because I’d read many good things about iA Writer’s latest Mac version (5.x), it had the lead from the beginning. Still, I gave fair shots to not only Typora and MultiMarkdown Composer but also Visual Studio Code, the code editor I already was using for HTML and CSS work on the site. Each of these other apps had strong merits but, sure enough, I chose iA Writer as the best fit.

So it would be Ulysses for long-form writing and iA Writer for the posts here. Easy peasy.

Or so it seemed for a few weeks.

Incidentally, as part of my getting to know iA Writer better, I even exported copies of my WIP from Ulysses to iA Writer’s default storage location, the iA Writer iCloud Drive folder. I then began working on the WIP in both apps across my Apple devices, using whichever one caught my fancy that particular day. As time passed, I figured out ways to recreate (or, at least, simulate) certain Ulysses features that iA Writer lacked2. And, with my growing adherence to the wisdom of keeping one’s writing in plain-text formats, I also enjoyed the resulting peace of mind that came from knowing I had a backup plan for the WIP if, for some reason I couldn’t yet imagine, I decided against continuing to be a Ulysses user.

So what exactly escalated this to an out-and-out decision to leave Ulysses at all, much less for iA Writer?

Coincidentally enough, it was one of the chief reasons I’d chosen Ulysses over Scrivener the previous year: an uneasiness over the incumbent app’s ability to sync files to The Cloud from among my Apple devices. In Scrivener’s case, the targeted cloud is Dropbox; for Ulysses (as for iA Writer), it’s iCloud.

That sync’ing feeling

One Sunday afternoon, I opened Ulysses on my Mac, expecting to have a perfectly normal writing session, and noticed the Ulysses Library didn’t have my WIP’s latest changes, which I’d made on one of my iOS devices earlier in the day.

In fact, as I quickly saw to my growing consternation, it didn’t have the changes from the last two or three days of my work in iOS; and all the WIP’s most recently edited sheets (files in the Ulysses Library) showed the little “iCloud activity” icon in their listings. That icon normally appears only for a second or two and then goes away, but this time it was hanging around.

Sync was stuck on my Mac’s installation of Ulysses, and had been that way for days.

Screen capture from Ulysses showing iCloud icon, indicating ongoing sync

When this little cloud icon (highlighted in the yellow circle) just sits and sits and sits in the Ulysses sheet synopsis and the timestamp doesn’t change, even though you edited this file days ago on another device — Houston, we have an iCloud sync problem.

Yet, other apps seemed to be doing fine and there were no signs of trouble in the Mac Finder or even iCloud itself, according to Apple’s status page.

I started searching frantically for a way to resolve this. After a while, I ran across instructions for viewing the iCloud log. When I did so, indeed, I saw error messages indicating that the Mac’s Ulysses Library wasn’t syncing with iCloud.

I then found a suggested fix: create a new group (a folder-like item in the Ulysses Library), pull up a backup of the sheets that aren’t sync’ing, and move them to the new group. I did; and, suddenly, sync was running normally again within Ulysses on my Mac.

Fair enough, I figured, as my blood pressure gradually settled down.

But, during my search for answers, I’d had one of those “Can’t unsee it” moments.

“A long, hard, awkward stare”

On the same forum page where I’d found the fix, multiple other posters said they, too, had gone through similar Ulysses/iCloud SNAFUs — in some cases, years ago.

To me, that meant what I’d experienced was essentially a known bug in the very Ulysses/iCloud seamlessness that I’d celebrated in blissful ignorance for months.


Several posters even made it clear that, as a result of this problem, they no longer trusted Ulysses with their writing.

Then, further down the page, I found a follow-up from the original poster, and some of his words hit all too close to home with me:

I’m still using Ulysses. But I’ve been giving a long, hard, awkward stare at iA Writer over the past few days. . . . Partially because I have The Fear now. . . . Partially because iA [Writer] matches the features in Ulysses that I use, and I don’t use many of the features in Ulysses. . . . And frankly, I’m worn out from fiddling around with apps. Plain-text might finally allow my soul to rest.

Ouch. Oof. “Down goes Frazier.”

Had my trouble been a one-shot deal, an isolated incident, that would’ve been one thing. But the comments on that page and others told me that this, in fact, was a glitch that numerous Ulysses users had encountered over the years.

Since sync’ing is one of those cases where “failure is not an option,” I now had to decide whether to continue storing my work within this app which, heretofore, I’d trusted completely.

And, in case you’ve decided I was being too hasty, that I was letting one odd occurrence and some random complaints on the web sour me on a perfectly fine app: that Sunday afternoon wasn’t the end of the trouble. I continued to suffer various types of a Ulysses/iCloud “failure to communicate,” and even lost some work as a result. Moreover, none of my other apps — most especially iA Writer, with its support for Open in Place as well as its fully transparent file storage in the Finder and the iOS Files app, as opposed to the workings of the obscurely located Ulysses Library3 — had so much as a whisper of trouble dealing with iCloud.

Besides: having to evaluate whether a late-2010s writing app will store and sync your content reliably is like having to evaluate whether an NFL running back can carry the ball without fumbling: that’s his frickin’ job.

A few days after the initial scare, I consulted a fellow writer, blogger, and Ulysses user whose opinions I trust greatly, and asked him whether he’d run into similar problems with Ulysses/iCloud sync. He said he had, multiple times, and that was a major part of why he was considering ditching Ulysses when his own subscription neared its end in a few months.

Mine was due for renewal around the end of May, so decision time was nearing.

The arrival of Ulysses 15 on March 11 — admittedly an impressive release with a lot to offer — didn’t change my mind. The new and improved features were great. The ongoing risk to my content4 wasn’t.

It’s not me; it’s U

Trying to find a way not to dump Ulysses, I sent questions to Ulysses Support asking about possible ways around the problem. Mind you, I didn’t couch it in a “If I don’t like your answers Imma stop using your app” way, so perhaps they’d have responded with more urgency if I had. (Then again, who am I kidding?) In essence, my question was: what if I just used Ulysses’s External Folders feature and pointed it to a regular folder out on iCloud Drive, thus getting around the proprietary Ulysses method? No, stuff wouldn’t be in the Ulysses Library and getting all the capabilities that go with it, but they would be getting sync’d with iCloud as they should be. Or, at least, so I figured.

However, my gambit was doomed to failure because, as one of the very nice people at Ulysses Support told me, that wouldn’t work with iCloud:

Ulysses for iOS currently doesn’t support any other syncing backends but the one for Dropbox.

Thus, not only would I have to lose most of the coolness of Ulysses but I’d also have to rely on Dropbox again, when I’d already decided to make iCloud and iCloud Drive my go-to combo for sync, and so far only Ulysses was giving me trouble on that score.

Yet another nail in the Ulysses sub’s coffin.

But it was hard to let go. Even as late as a couple of weeks ago, I found myself posting this on Twitter:

I may be crazy, but have been stress-testing Ulysses and am giving it one more chance **not** to eat my stuff before I pull the plug on my subscription (ends in late May). It’s hard to quit an app that makes writing such a pleasure, even one with known issues. #DontFailMeNowBigU

And, almost as if it had gotten the message, Ulysses was good as gold across my devices — until this morning.

Then, after doing some WIP edits in Ulysses on my iPad last night and confirming that they’d transferred smoothly and nearly instantaneously over to the iPhone across iCloud, I opened up Ulysses on the Mac so I could copy the latest edits over to iA Writer just to be safe, as I’ve done throughout this “stress test.”

Last night’s edits weren’t there; the last stuff there was from the night before last, my most recent editing session on the Mac. I waited. And waited. I wasn’t about to touch anything at this point, lest I cause any conflicts. Finally, nearly five minutes later, the newest edits began popping up on the Mac, except that their timestamps were from right that moment, when they’d appeared in the Mac version, not when I’d actually last edited them.

I just sat there a minute, thinking about what I’d just witnessed and what it meant. Finally, I muttered, quietly and sadly, “Well, sir, that’s all she wrote.” I got those files safely copied over to iA Writer and — for the last time — closed Ulysses.

Note from 2019-05-04: I’ve since learned that the behavior re the timestamp turns out to be common for so-called “shoebox” or “central-library” apps like Ulysses and, for that matter, Apple’s own Notes and Photos apps. So, while I considered it the Smoking Gun at that point, now I doubt that. This doesn’t explain the earlier business with the sync not happening for days, of course, but I’ve also learned of numerous similar reports from users of “shoebox” apps so, while that doesn’t make it okay, it does suggest the fault isn’t necessarily that of Ulysses. Again, will update with more info when I can.

Shortly after that, I killed the Ulysses subscription on which I’d embarked with such high hopes and expectations last May. (Of course, it’s still valid until the expiration date a few weeks off, but now I don’t care.)

Incidentally: at one point during the last few weeks of agonizing over this, I found interesting reading in the Ulysses FAQs regarding iCloud sync, especially given my responses to each:

  • iCloud enabled on all my devices under my Apple ID? Yep.
  • iCloud setup definitely working on each device? Yep.
  • Bumping up against my iCloud storage limit? Hardly. Not using even a quarter of it since upping my sub to the two-terabyte tier in February.
  • Firewall causing issues? Nope.
  • Restarted everything involved? Yep × three (at least).
  • Sure the sheets I want to sync are in the right place in Ulysses? Definitely.
  • Properly connected to the Interwebz? Yep × three again.
  • Patient? Yeah, but there’s a limit, man.
  • iCloud status good? Yep.

It struck me that those seemed to constitute a long string of “It’s not us, it’s [you and/or iCloud]” things to evaluate.

No, in fact, it’s not me. Or iCloud. It’s U, Big U.

However, that was probably just how my wandering mind took them; because, by the time I got to the end of the FAQs, where Ulysses was concerned, I already had my hand on the proverbial Door You Shouldn’t Let Hit You in the Rear on Your Way Out.

The geek’s prerogative

Screen capture from iA Writer app

Ladies and gentlemen, the winner (for now): iA Writer.

For now, iA Writer is the winner for my heart and mind when it comes to picking a writing app. I use it to write both the WIP and posts like this one, and I like it more every day. I share the feelings of those who say it actually makes them want to write something just so they can use it, especially its iOS version, which I prefer greatly to those for Scrivener and Ulysses5 — and that’s high praise, because each of those is outstanding in its own way.

Still, don’t mistake this for unbreakable devotion. I claim the geek’s prerogative to switch apps at a moment’s notice whenever something demonstrably better appears.

To be sure, many don’t find iA Writer a suitable replacement for Ulysses. Use cases vary widely. It’s just that my writing needs are relatively simple. I write the stuff for this site and I write my fiction, and iA Writer is more than enough app for both. For more complicated needs, such as screenwriting or academic writing, iA Writer may not be one’s best option.

For me, for now, it will do. And, just in case I haven’t made my meaning sufficiently clear . . .

One important thing I’ve gained through the transition to Markdown-flavored plain text is tremendous freedom for the future. If the day comes that iA Writer either ceases to exist or simply winds up on my bad side one day for reasons I can’t currently predict — well, there’s a great, big world of Markdown-savvy apps out there, with more on the way.

So, yes, iA Writer, for now, I welcome your icon to the center positions on the docks of my Mac and iPad, and also to a presence in the Honored Four apps always visible at the bottom of my iPhone home screen. Just be sure you keep earning your presence there. Above all, don’t get too comfortable.

Your predecessors did, and look what it got them.

  1. Sometimes there are disparities between the original Markdown files and how they translate to HTML, so it’s best to catch those in a local instance before you publish to the real site, and thus I was having to do that “dance” quite often during the editing process. ↩︎

  2. For example, iA Writer lacks the commenting features available in Ulysses through the use of either %% or ++ as markup characters; however, because Markdown allows the insertion of HTML and CSS, I simply replaced Ulysses comments with HTML-style commenting that <!-- looks like this --> and is invisible when exported to other file formats when that’s necessary. Pretty cool, huh? ↩︎

  3. For further details on how and where the Ulysses Library stores files, see: “The Library, and File Management” in this article by Marius Masalar. (In the original version of this post, I also referenced an excellent 2017 Ulysses review by Chris Rosser, but it no longer appears on his website.) ↩︎

  4. The glitchiness continued even after I upgraded to Ulysses 15, in case you’re wondering whether I was sticking with an older, possibly problematic version. Similarly, my devices were — and always are — on the most currently available versions of both macOS and iOS. Trust me: especially in this time of one zero-day exploit after another, I am not one of these “Ooh, I don’t believe in using the latest-and-the-greatest” people. ↩︎

  5. To be fair, I’ll mention one annoying problem in iA Writer for iOS: many times, when you attempt to select text, the cursor suddenly goes all caffeinated on you and wildly selects far more than what you intended. It appears to be a known bug which I hope the iA folks will fix soon. ↩︎