Note-Taking Apps That Work Until They Suddenly Do Not

Table of Contents

1. Why shared pages in Notion break task handoffs midweek

The recurring problem with Notion isn’t what it does — it’s what it forgets to tell you when it stops doing it. I had a shared Notion database for onboarding tasks, lightly templated and passed between account managers. Every Monday, it got a fresh copy. By Wednesday, one person’s changes were gone. It wasn’t sync lag. It was version collision from someone duplicating the old template page instead of using the synced block version.

Here’s how that breaks things: Notion doesn’t force a page to be linked to its original once duplicated. Duplicating strips it of its sync context — and if the template still has formal relations (think rollups, filtered views, now-empty relation fields), the freshly copied pages inherit the inputs, but no longer update the parent dashboards. No warning. It just sits there looking like it works.

“Duplicate from the three-dot menu, not with CTRL+D” was actual internal policy for a bit.

If you’ve got people jumping between sidebar templates and toggling old links sitting in Slack threads, someone’s going to unthread the system by accident. Bonus fail: Synced blocks get entirely removed if anyone resets the block source. That setting doesn’t have a prompt. They can just… do it. It vanishes. No undo.

2. What broke in Obsidian when I enabled community plugins too early

The day I turned on the Calendar plugin before setting a base folder for my daily notes, everything went off the rails. The plugin assumed the default area was my Vault root until I created a subfolder. For two months, any links pointing to existing dailies were subtly incorrect if the file already existed in a different substructure.

It wasn’t immediately obvious. The backlinks panel showed connections. But it turned out those were string matches — not resolved links. A note dated “2025-04-10” inside /Notes/Daily/ was being connected to a ghost note in root. Obsidian was technically accurate. But plugins like Dataview depended on full path references.

When I finally connected the dots, it was one line of YAML in the plugin config:

{ "defaultNotePath": "Daily/" }

…and after that, all my templates began pointing cleanly. But two months of meetings had already sunk into a malformed note tree, and the migration CLI tool didn’t catch non-linked files since filenames were technically valid.

The unspoken catch: Obsidian’s UI won’t warn you about escaped file collisions.

3. How synced tags between Apple Notes and Reminders quietly misfire

Apple shipped tag syncing across Notes and Reminders with an iOS update sometime mid-cycle. If you used #projectX in Notes, your Reminders could search for the same. Simple… until you bulk-edit tags in one app and expect consistent behavior in the other.

They’re not actually the same system.

Notes uses a metadata-based tag stack per file header – think hashes stored with the file. Reminders uses inline token parsing. Changing or deleting a tag in Notes updates that file’s metadata, but doesn’t signal a system-wide tag rename. Reminders sees the tag string as one-off text. So if you rename #projectX to #projX in Notes, Reminders doesn’t retroactively rename it. It becomes a ghost tag — still searchable, still indexed, no longer connected.

The “aha” that made this click: Searching #projectX in Spotlight surfaced the old tag in Notes, but not in Reminders. That’s because the indexing backend changed in iOS 17, and Reminders didn’t rebuild the index unless a manual tag sort order was changed once.

Literally dragging a tag up in the list forces a rebuild.

Feels intentional, but it’s not documented anywhere.

4. When Evernote’s AI suggestions made my search terms worse

Evernote brought in semantic search suggestions a few updates ago, without much fanfare. Light gray suggestions below your search bar. Great in theory. In practice, I searched “client onboarding funnel,” and the top suggested term was… “marketing calendar.”

The twist: clicking the suggestion executes it fully, but doesn’t log your real query. That means recent searches showed only “marketing calendar,” not what I wanted — and their AI tuning gets worse from feedback loops treating accepted suggestions as accurate.

The real bug though? Once you click a suggestion, you can’t “go back” to your original string unless you remember and re-type it. Cmd+Z doesn’t affect search inputs. Arrow keys sometimes break in Safari’s PWA mode, too — if you reinstall Evernote via Stage Manager, it seems to sandbox the input context until restart.

This made my note retrieval flow so unreliable I started copying search queries to a scratchpad. Not even as a joke. I would forget what I was actually looking for after tapping a suggestion that overcorrected.

5. The Airtable interface button that only works if you look directly at it

I set up an Airtable Interface with an “Add Task” button connected to an automation that inserts a linked record. Worked once. Then not again. Nothing broke visibly… it just didn’t fire.

Turns out: Interface buttons only execute if the browser is focused AND the record view is not in edit mode from a prior field click. If someone clicks a field next to the button and then clicks the button quickly? No dice. Airtable doesn’t throw an error, it just doesn’t trigger the automation.

This bit felt like black magic:

// Click context lost if field is partially focused
if (document.activeElement.tagName === 'INPUT') { fail(); }

I added a literal 300ms delay using setTimeout in a fake button-hijacking script just to maintain focus context. And no, this hack wouldn’t survive in production for others — but it taught me something useful about event bubbling inside Airtable’s React layer.

Here’s what finally made it predictable again:

Disable inline editing in that Interface section
Break buttons into separate component groups
Use views filtered to just one record at a time
Add a rich-text instruction area that resets mental clicks
Trigger automation on record creation, not button click

Every one of these things reduces risk of user interaction clobbering button context. But it still feels fragile.

6. When AI summaries in Notion hallucinate missing context tags

There’s something creepily confident about Notion’s new AI summary blocks. I dropped in my meeting notes around a product launch and used the “TLDR” block. Looked good — bullet points, good phrasing. Then my coworker asked why we were “moving away from channels for onboarding.” I had no clue what she meant. That wasn’t in the doc.

I dug into version history. The original notes only said: “possible Slack change — TBD after Danielle gives feedback.” That’s it. No decision, no plan. But the AI summary offered: “Team agreed to discontinue use of Slack channels for onboarding.”

It hallucinated consensus.

And here’s where it gets more annoying: regens didn’t fix it. Even regenerating with narrower text selection still extrapolated that same decision. I think it was leaning too hard on phrases like “team discussed” and “alternative” earlier, and combining implicit consensus where there was none.

The summary felt accurate. Until it wasn’t. And no one caught it because we had copied the bullets into our Monday doc verbatim.

Lesson: I now wrap AI summaries in a red callout box labeled “auto-generated not reviewed.” Not elegant, but it changes how people read it.

7. What breaks if you sync Bear and iCloud across macOS betas

I found this out the hard way during a macOS Sonoma Public Beta window. Used Bear for most of my ongoing personal and scratch notes. Synced tags and search beautifully — until I opened it on a second machine also running Beta 2. Suddenly, notes were doubling, with two separate copies of every note with slight character differences — some with underscores, others with em dashes.

This wasn’t Bear’s fault in isolation. It was iCloud’s metadata merge conflict logic on beta firmware. For app containers with unversioned notes, the rapid renaming inside Bear (e.g. title folding) created a new iCloud version on every edit save. That meant two paths for what the system thought were different notes.

Note slugs got desynced silently. Same title, different UUID.

It finally stopped when I unsynced Bear from iCloud for one device and reinstalled fresh. But I lost any changes made during the duplicate period because iCloud treats those UUIDs as independent files — and Bear’s restore doesn’t recognize both as the same note.

If you use Bear during beta cycles, export weekly. Zip and stash.