# my obsidian keeps crashing. the last time thi s happens is because some file was far too big for...
## Retrieval Notes
- Session id: `019d07f6-c522-7252-8cdc-758f0ba36e52`
- Source: `Codex raw session`
- Last activity: `2026-03-19T21:24:59.672Z`
- Model: `gpt-5.4`
- CWD: `/Users/nickyoung`
## My Notes
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## Conversation
### User
my obsidian keeps crashing. the last time thi s happens is because some file was far too big for the vault so it broke when ever it try to scan it (?)
### Assistant
I’m going to check the recent vault context first, then inspect the vault for unusually large files and recent additions that could make Obsidian choke during indexing.
### Assistant
I’ve got the CLI guidance loaded. Next I’m reading yesterday’s and today’s daily notes for continuity, then I’ll inspect Obsidian’s own view of file sizes and recent files instead of guessing from the filesystem alone.
### Assistant
The daily note folder has some stray files mixed in, so I’m switching to Obsidian’s own `daily:path` and vault API to avoid reading the wrong thing. After that I’ll ask Obsidian for the largest files in the vault and the most recently modified non-markdown files.
### Assistant
Obsidian’s CLI calls are themselves aborting, which makes the crash theory more plausible. The CLI isn’t giving us a clean API path right now, so I’m falling back to the filesystem to identify oversized files in the vault and likely recent offenders.
### Assistant
There are a few strong suspects already, and one stands out: a 144 MB plugin cache file inside `.obsidian`, updated today, plus a 201 MB conversation markdown file. I’m checking which of the biggest files changed most recently so we can isolate the likely trigger rather than moving random old archives.
### Assistant
I’ve narrowed it down to two very plausible triggers. I’m doing one more pass on the giant conversation file to see whether it’s just a long transcript or whether it accidentally contains dumped JSON/base64 that would make Markdown indexing especially ugly.
### Assistant
The giant conversation file isn’t a normal long transcript. It has only 50 lines total, which means one or a few absurdly long lines are carrying almost all 201 MB. I’m confirming which line blew up so we can target exactly the bad artifact.
### Assistant
I’ve got the smoking gun: one conversation note has a frontmatter `title:` line that exploded into a gigantic escaped string, and the metadata-extractor plugin then wrote a 144 MB cache from it. I’m checking whether that plugin is currently enabled so I can give you the safest recovery order.
### Assistant
I found a very likely cause.
The strongest culprit is [2026-03-17-codex-019cfdd9.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-17-codex-019cfdd9.md). It is 201 MB, but only 50 lines long, which means one line is enormous. The bad line is the frontmatter `title:` near [line 5](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-17-codex-019cfdd9.md:5): it has exploded into a gigantic escaped string of backslashes. That is exactly the kind of malformed markdown/frontmatter blob that can make Obsidian hang or crash while indexing.
There’s also a secondary artifact at [metadata.json](/Users/nickyoung/My%20Obsidian%20Vault/.obsidian/plugins/metadata-extractor/metadata.json), which is 144 MB and was updated right after that note. That looks more like fallout than the root cause. Interestingly, `metadata-extractor` is not currently listed in [community-plugins.json](/Users/nickyoung/My%20Obsidian%20Vault/.obsidian/community-plugins.json), so the bad conversation file itself is the main thing I’d target first.
Safest recovery order:
1. Quit Obsidian completely.
2. Move [2026-03-17-codex-019cfdd9.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-17-codex-019cfdd9.md) out of the vault temporarily.
3. If Obsidian still struggles, also move [metadata.json](/Users/nickyoung/My%20Obsidian%20Vault/.obsidian/plugins/metadata-extractor/metadata.json) out temporarily so it can be regenerated or ignored.
4. Reopen Obsidian and see if the vault stabilizes.
I haven’t moved anything yet because that changes vault contents. If you want, I can quarantine those two files for you now in a reversible way.
*Quel file sembra corrotto più che semplicemente grande, e la riga del titolo è quasi certamente il punto in cui l’indicizzazione va in crisi.*
### User
any idea what could have caused that?
### Assistant
Most likely: a broken export or sync step wrote unescaped content into YAML frontmatter.
Why I think that:
- [2026-03-17-codex-019cfdd9.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-17-codex-019cfdd9.md:5) has a `title:` field that turned into one absurdly long quoted string full of escaped backslashes.
- The file is 201 MB but only 50 lines, so this was not “a long conversation” in the normal sense. One field ballooned catastrophically.
- Right after that, [metadata.json](/Users/nickyoung/My%20Obsidian%20Vault/.obsidian/plugins/metadata-extractor/metadata.json) got huge too, which fits Obsidian or a plugin trying to parse and cache the bad note.
Plausible mechanisms:
- A conversation-sync plugin or script serialized the title incorrectly, probably re-escaping an already-escaped string over and over.
- A recursive bug: something may have taken a whole prior document or JSON blob and stuffed it into the `title` field instead of a short title.
- A failed retry/append loop: the sync process may have kept rewriting the same field repeatedly after an error.
- Less likely, but possible: another tool edited the frontmatter while the conversation exporter was writing, producing corrupted YAML.
What seems less likely:
- “Just a file that was too big.” The evidence points more to corruption than ordinary size.
- A normal screenshot, PDF, or audio attachment. Those are large, but they don’t usually break markdown indexing in this way.
So my best guess is: the `agent-client`/Codex conversation export path produced one malformed note, and then Obsidian’s indexer/plugins made the situation worse by trying to ingest it.
If you want, I can inspect the surrounding `agent-client` session files and config next to narrow down which component likely wrote the broken frontmatter.
*La causa più probabile è un errore di serializzazione: non la grandezza in sé, ma un campo `title` scritto in modo ricorsivo o corrotto.*
### User
"So my best guess is: the agent-client/Codex conversation export path produced one malformed note, and then Obsidian’s indexer/plugins made the situation worse by trying to ingest it.
If you want, I can inspect the surrounding agent-client session files and config next to narrow down which component likely wrote the broken frontmatter." please
### Assistant
I’m going to inspect the `agent-client` plugin files, the matching session JSON, and neighboring conversation exports to see whether the bad `title` came from the session source data or got introduced during markdown export.
### Assistant
The plugin settings look normal, and stored titles there are short/truncated. That points away from a bad saved title in `data.json` and toward either one corrupt session JSON or a bug in the markdown export step for that session.
### Assistant
One important clue: the broken session id `019cfdd9...` does not appear in the current `agent-client/sessions` folder or in `savedSessions`. That suggests the malformed note may not have come from the current `agent-client` plugin at all, or it came from an earlier/export-only path whose source session file is gone.
### Assistant
The neighboring Codex export looks perfectly normal, including `source: "codex-jsonl"`. So the bad file wasn’t produced by a completely different format; it looks like the same export family with one field going off the rails.
### Assistant
A clearer pattern is emerging: these Codex exports seem to derive `title:` from the opening user content, sometimes including markdown links and system preamble text. That makes the title-generation path itself a likely weak point, especially when the opener contains odd escaping or injected context.
### Assistant
I dug into the surrounding files, and the likeliest culprit is narrower than “Obsidian” or even “agent-client” in general.
My best read is this:
- The broken note is in the Codex export format, not the normal `agent-client` export format. You can see that in [2026-03-17-codex-019cfdd9.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-17-codex-019cfdd9.md:2) with `type: codex-session`, `source: "codex-jsonl"`, and `originator: "codex_cli_rs"`.
- The current `agent-client` plugin state in [data.json](/Users/nickyoung/My%20Obsidian%20Vault/.obsidian/plugins/agent-client/data.json) stores short, sane titles. The bad session id `019cfdd9...` is not present in `savedSessions`, and there is no matching live session JSON under `.obsidian/plugins/agent-client/sessions/`.
- Other recent Codex exports are normal, but they reveal a fragile pattern: the `title:` is being derived from raw opening content, sometimes including markdown links and preamble text, as in [2026-03-19-codex-019d056f.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-19-codex-019d056f.md:5) and [2026-03-19-codex-019d054c.md](/Users/nickyoung/My%20Obsidian%20Vault/Conversations/2026-03-19-codex-019d054c.md:5).
- In the broken file, the `title:` line starts as a giant escaped string of backslashes and only much later reaches the real user text. That is classic “escaped repeatedly on rewrite” behavior, not “user typed a huge title.”
So the most likely component is:
- the Codex raw-session-to-Markdown export path
or
- a sync/import layer that rewrites Codex session metadata into frontmatter
Less likely:
- `agent-client`’s normal saved session store
- a random attachment or large binary file
- Obsidian itself generating the corruption
The strongest hypothesis is:
1. A Codex session title was generated from raw opener/context text.
2. That title already contained quotes, markdown, or escape-heavy content.
3. A serializer/exporter rewrote it multiple times, re-escaping the existing escaped string each time.
4. The resulting malformed `title:` ballooned the note, and then Obsidian plus `metadata-extractor` amplified the damage by indexing it.
One extra clue in that direction: nearly all the healthy Codex exports have `title:` lines of about 109 characters, which looks like a truncation routine. That means there is definitely an automated title-generation step in this export family, and that is the exact area I would distrust here.
So if we’re assigning blame as precisely as possible, I’d phrase it like this:
- probably not the `agent-client` session store itself
- probably yes the Codex conversation export/import pipeline that produces `codex-session` markdown notes
- with a likely bug in title generation or repeated escaping during rewrite
If you want, I can do the next practical step and trace which local script/plugin/process is actually writing these `Conversations/2026-03-*-codex-*.md` files so we can stop it happening again.
*La pista più forte non è il plugin in generale, ma il passaggio che trasforma una sessione Codex grezza in frontmatter Markdown con un `title` generato automaticamente.*
### User
"If you want, I can do the next practical step and trace which local script/plugin/process is actually writing these Conversations/2026-03-*-codex-*.md files so we can stop it happening again." that would be good, but am I going to be led nto making brittle changes about these things.? or is this a normal thing.
### Assistant
Not necessarily. Tracing the writer is normal diagnostic work; brittle changes only come in if we jump too quickly from “we found the symptom” to “let’s hand-edit the whole pipeline.”
What I’d suggest is a low-risk order:
1. Identify which process is generating the `codex-session` notes.
2. Confirm whether the bug is in title generation, escaping, or repeated rewrites.
3. Prefer a narrow guardrail over a structural rewrite.
The kind of fix that would be normal and not especially brittle would be something like:
- cap exported title length hard
- strip newlines/markdown links from title candidates
- refuse to write absurd frontmatter values
- fall back to `"Untitled Session"` if the title sanitizer fails
That is pretty standard defensive programming, not a fragile one-off hack.
What would be brittle is:
- lots of vault-specific regex patches
- special-casing this one exact session id or exact phrase
- layering multiple cleanup scripts over the exporter without identifying the true writer
So yes, I think it’s worth tracing, and no, that doesn’t automatically commit you to some delicate house-of-cards fix. The sensible version of this is: find the writer, add one boring safety check in the export path, and stop notes from becoming pathological.
If you want, I’ll do the tracing next in read-only mode first and then tell you whether the likely fix looks clean or hacky before changing anything.
*La soluzione migliore sarebbe una piccola difesa generale nel punto di esportazione, non una toppa fragile costruita su questo caso singolo.*