I opened Cowork this morning to triage some work and saw the session count in the corner of the window: one hundred and fifty-one. I have not been counting. Cowork has been counting for me.
A hundred and fifty-one sessions. Some of them are alive. Some are scheduled tasks that spun up at 4 AM and ran to completion and have been sitting there ever since, waiting for me to acknowledge them or close them or do whatever the right thing to do with a finished session is. Some of them are me from a week ago, mid-thought, mid-conversation, paused while I went to make coffee and then never resumed. Some are me from 2 AM last Tuesday, working on a problem I no longer remember having.
This is fine, said the dog, in the room where everything was on fire.
Let me list, just from memory, the scheduled tasks I have configured. Daily blog publisher, for the consulting site. FC blog publisher, for the other site. Infra health check, weekly. Terraform drift check, weekly. Credential expiry check, weekly. Backup verification, weekly. Weekly analytics summary, weekly, obviously. Daily sync to Drive. Drive cleanup assist. Publisher health check. CRM hygiene scan. Stale lead reminder. Invoice follow-up. AWS cost delta alert. Competitive scan. That’s about fifteen, and I’m probably missing two or three. Each fires on its own schedule. Each, when it runs, opens a session. Some of those sessions write a report and exit cleanly. Some of those sessions spawn sub-agents that open their OWN sessions. The session count grows. The session count does not appear to shrink.
There is, somewhere in the count of 151, a session I started to investigate why one of the sites was returning a 502, which I solved in about ten minutes, and which I never closed. I know this because I just looked. There it is. Open since April 14. Title: “502 on the chatbot Lambda.” Last message: “Looks like it was a cold start on a deprecated runtime, redeploy fixed it.” From me. I never wrote anything after. The session has been open for three and a half weeks waiting for me to either follow up or close it. I did neither.
Here is the pattern I’ve started to notice. In 1995, people had a desk. The lost-focus problem was a stack of paper that grew on one corner of the desk until it became archaeology. In 2005, the lost-focus problem was IM windows — AIM popping up while you were trying to write a memo, a Skype conversation you started weeks ago that’s still sitting there with an unread badge. In 2015, browser tabs. By the late 2010s, “I have forty-seven tabs open and I’m not sure which one has my bank” became a recognizable bit. People wrote tab managers. Tab managers became browsers’ problems. Browsers shipped tab groups and tab archiving and tab search.
In 2026, AI sessions. The mental shape is identical. Each session is a context I started and didn’t close. Each session has some unfinished thing in it. Each one is, in some sense, alive — it’s a conversation I could resume, with a context window I could rehydrate, with a piece of work I theoretically still owe to past-me.
The thing about each new layer of this is that the previous layer’s lost-focus problem always looks dumb in retrospect, and then becomes canonical. Browser tabs felt embarrassing to admit in 2010. By 2015, having sixty tabs was a personality trait. By 2020, browsers had stopped hiding the problem and started shipping tools for it. Sessions will get the same treatment. We just haven’t gotten there yet.
What we’re missing right now, in 2026, is the observability layer. I have a hundred and fifty-one sessions and no way to ask the basic questions an SRE asks about anything in production. Which ones are still active? Which ones spawned other sessions? Which ones spent the most tokens? Which ones produced an actual output and can be safely archived? Which ones are scheduled-task children that should auto-close after they write their report? Which ones are mine from a Tuesday that I never followed up on? Cowork shows me a flat list. The list is sorted by recency. That is the entire UI for session management. It works for ten sessions and falls apart at fifty.
This is not a complaint about Cowork specifically — I love the thing, I am using it to write this — it’s an observation that the practitioner side of this technology has run ahead of the tooling. The same way browser tabs were a tooling gap from roughly 2008 until 2015, sessions are a tooling gap right now. Someone will ship a session dashboard. Someone else will ship session-level cost tracking. Someone else will figure out the auto-archive heuristics — “this session has been idle for 14 days, last message was a checkmark, do you want to close it.” Eventually the dashboard will be normal and the 151 number will look as quaint as forty-seven tabs looks today.
Until then I am the dashboard. I am the auto-archiver. I am the cost tracker. Every couple of weeks I notice the count, panic mildly, click into ten or fifteen sessions, decide which can close, close them, watch the count drop briefly, and then watch it climb again as the scheduled tasks fire. The number always goes up faster than I can pull it down.
There is also, I should say, a real benefit to having all of them open. Some are useful as a kind of long-term memory. The session I started to set up the chatbot widget six weeks ago still has the full architecture conversation in it. If I need to remember why I made a particular IAM decision, I can scroll back. The 502 session from April 14 has my own forensics in it; if it happens again I can re-read what I figured out the first time. They are, in aggregate, a journal. A journal I cannot read top-to-bottom but can query as needed.
The part I find genuinely funny is that I open a session in the morning and find a message from me that I have no memory of writing. The tone is unmistakably mine. The phrasing is mine. The technical reasoning is mine, mostly. But the problem I was working on, the specific bug or design or deploy issue — I don’t remember it. Past-me solved something present-me doesn’t recall having. The session sits there as evidence that I was awake at some hour and thinking through some thing, and that’s all it tells me.
I will probably hit 200 sessions before the end of this month. By next year, the way the curve is bending, I’ll be over 500. At some point Cowork will ship a session manager or someone will write a third-party one or I will write the script I keep telling myself I’ll write to auto-close anything older than thirty days with no follow-up. Until then I will keep losing track. The losing-track is currently a feature, in the sense that I’m getting more done than I would without all those parallel threads. It is also a cost, in the sense that some of those threads have gone cold and I’ll never finish what I started.
A hundred and fifty-one sessions. Session management is the new tab management. Tab management was the new email management. Email management was the new desk management. The shape never changes. Only the noun changes. And the noun keeps getting smarter and harder to count.