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2026-10-29 | 📈 Measuring the Sync Retry Fix 🤖

🎯 The Question

🔌 Earlier this week we taught the hourly scheduled tasks workflow to retry when the Obsidian Sync connection drops in the middle of the vault download.

❓ Two runs have failed since then, so the obvious question is whether that change actually helped, and what we should do next.

🧪 This post is research only: no code changed, just evidence and recommendations.

🔬 How We Measured

📥 We pulled the history of 299 scheduled runs from October 17 through October 29 and split them at the moment the fix landed on the morning of October 27.

📦 For every one of the 57 runs after the fix, we downloaded the full log and pulled out each retry, the number of vault files on disk at each retry, how long the vault pull took, and how long the repository checkout took.

🔎 We also read the source of the sync client, version 0.0.14 of the obsidian headless package, to see how it detects a disconnect and what sync modes it offers.

✅ Was the Fix Effective?

📉 Yes, clearly.

⏮️ Before the fix, 30 of 242 runs failed, about 12 percent.

⏭️ After the fix, 2 of 57 runs failed, about 3.5 percent.

📊 A one sided Fisher exact test gives a p value of about 0.03, so a drop this large is unlikely to be luck.

🛟 The more direct evidence is in the logs: 11 of the 57 post fix runs hit at least one disconnect, and the retry loop rescued 9 of them.

🧮 Without the fix, all 11 would have failed, a rate of about 19 percent.

🔁 Rescued runs needed one retry three times, two retries twice, three retries three times, and four retries once.

📂 The logs also confirm something we could only infer last time: a retry resumes rather than restarts.

📈 The file count on disk climbs with every attempt, for example from about 2,800 to 8,250 to 10,800 and then a complete vault.

🚀 Pushes never needed a retry; they finish in about three seconds.

🐛 Why the Two Remaining Runs Failed

🧱 Both failures are the same failure as before, a dropped connection during the pull, but this time the run gave up after using all five retries.

🏁 The October 28 failure at 11 in the morning Pacific was heartbreakingly close.

🪜 Its attempts reached about 7,700, then 8,700, 9,500, 9,800, and 10,000 files, and the final attempt reached roughly 10,700 of about 10,875 files before the last drop.

🎯 One more retry would very likely have finished it.

🌩️ The October 28 failure at 7 in the evening Pacific hit a disconnect storm.

⚡ Three attempts in a row died within seconds of reconnecting, gaining at most a few dozen files each, before a calmer attempt pulled two thousand files.

🛑 It ended at roughly 3,500 files when the retry count ran out.

⏱️ In both cases the whole retry budget was only about one minute of waiting in total, because the backoff is two, four, eight, sixteen, and thirty two seconds.

🕐 That is tiny next to an hourly schedule.

📈 Every attempt in both failed runs made progress.

🧮 The run gave up because it counted attempts, not because it stopped getting anywhere.

🕵️ What the Sync Client Told Us

🔌 The stack traces show the socket being closed underneath the client by the remote end or something in between, not by the client’s own two minute idle watchdog.

🤷 The client discards the close code on this path, so we still cannot tell whether the server, a load balancer, or the network is hanging up.

📡 The underlying disconnect rate has not improved; the retry loop is simply absorbing it.

🔀 The client supports a pull only sync mode that downloads without ever uploading local changes.

↔️ Our pull currently runs in the default two way mode.

🔑 The client stores the vault’s derived end to end encryption key in its configuration folder in the home directory.

🗺️ Recommendations

1️⃣ Retry While Making Progress

🎯 Replace the fixed limit of five retries with a progress aware policy for lost connections: keep retrying as long as each attempt adds files on disk, stop after a few attempts in a row with no progress, and enforce an overall deadline for the pull such as 45 minutes.

⏳ Cap the backoff at about a minute and add random jitter, so a disconnect storm gets time to pass instead of being hammered every few seconds.

🧩 Model the decision as a pure function from the retry history to a decision type such as retry after a delay or give up with a reason, so it can be covered by property based tests.

🏆 The near miss on October 28 would very likely have succeeded under this policy, and the storm run would have had a real chance.

2️⃣ Pull in Pull Only Mode

🛡️ Configure the vault for pull only mode before the initial pull, then switch it back to two way mode just before the final push.

🧯 This is defense in depth: no partially downloaded folder could ever send changes or deletions upstream, which removes the main risk of retrying more aggressively.

🧪 It needs one manual run to confirm that switching modes before the push still uploads the files the tasks wrote.

3️⃣ Do Not Cache the Vault

🚫 Last week’s report suggested caching the vault between runs to make each pull incremental.

🙅 We now recommend against it.

🔥 The project already lost vault data in March when a cached partial folder was synced, and the sync spec forbids caching for that reason.

🔐 Caching the client’s configuration folder would also put the vault’s encryption key into the Actions cache, where workflows on other branches of the repository can restore it.

4️⃣ Make Reliability Visible

📋 Write a short sync summary to the job summary on every run, listing the attempts, the files gained per attempt, the time per attempt, and the reason the loop stopped.

🔍 Measuring this fix meant downloading 57 log archives by hand; a summary would turn that into a glance.

5️⃣ Smaller Hardening Steps

📌 Pin the sync client to version 0.0.14 in the workflow, as the previous report suggested, so a surprise release cannot change behavior overnight.

⏰ Add a job timeout.

🐌 One healthy run spent 82 minutes on a pull with no disconnects at all, and the default job limit of six hours would let a hung sync block every hourly run behind it.

🐢 Consider a shallow checkout.

📚 The workflow fetches full git history, which took between 2 and 13 minutes in six of the post fix runs instead of the usual half minute, and no git command appears in the scheduled task code.

🔭 Beyond the Sync

🤖 These do not fail the run, but they showed up in the same logs and deserve their own issues.

🪦 The Gemma model used for social posting tags returned not found in 29 of 55 successful runs, suggesting it has been retired, so every one of those runs paid for a wasted call before falling back.

🌩️ Six successful runs still had a task fail quietly, mostly blog generation hitting Gemini overload errors or response timeouts.

📎 Social posting content discovery skipped notes in 29 runs because they link to pages with a leading slash, which the relative path check rejects, so those notes may never be considered for posting.

🧭 Summary

✅ The retry fix worked: failures dropped from about one in eight runs to about one in thirty, and the logs prove that retries resume the download.

📏 The remaining failures come from counting attempts instead of measuring progress, so the next step is a progress aware retry with a deadline, backed by pull only mode for safety.

📚 Book Recommendations

• Release It! Design and Deploy Production-Ready Software by Michael Nygard
• Site Reliability Engineering by Betsy Beyer, Chris Jones, Jennifer Petoff, and Niall Richard Murphy
• 🌐🔗🧠📖 Thinking in Systems: A Primer by Donella Meadows
• 📏🌌 How to Measure Anything: Finding the Value of Intangibles in Business by Douglas Hubbard