diff --git a/cli/commands/update/root.go b/cli/commands/update/root.go
index e609abf8..de2e53df 100644
--- a/cli/commands/update/root.go
+++ b/cli/commands/update/root.go
@@ -24,6 +24,7 @@ func Run() {
 	updateBrew()
 	updateClaude()
 	updateDevbox()
+	updatePi()
 	updateSolargraph()
 	reshimAsdf()
 	install.Call("vim")
@@ -92,6 +93,15 @@ func updateDevbox() {
 	run.Verbose("devbox version update")
 }
 
+func updatePi() {
+	if err := run.Silent("which pi"); err != nil {
+		log.Info("pi.dev not installed, skipping")
+		return
+	}
+	log.Info("Updating pi.dev")
+	run.Verbose("pi update")
+}
+
 func updateSolargraph() {
 	log.Info("Updating solargraph gem")
 	run.Verbose("gem update solargraph")
diff --git a/openspec/changes/archive/2026-09-25-add-pi-self-update/proposal.md b/openspec/changes/archive/2026-09-25-add-pi-self-update/proposal.md
new file mode 100644
index 00000000..e5da29e3
--- /dev/null
+++ b/openspec/changes/archive/2026-09-25-add-pi-self-update/proposal.md
@@ -0,0 +1,22 @@
+# Change: Update pi.dev during `dots update`
+
+## Why
+
+`dots install pi` only installs `pi` when it's missing (`which pi` short-circuits the
+installer) and is never called by `dots update`. Once installed, pi.dev's own binary never
+gets refreshed by dots — the user has to remember to run `pi update` by hand. Every other
+managed tool (Claude Code, Devbox, Homebrew, solargraph, asdf shims) is kept current by
+`dots update`; pi.dev should be too.
+
+## What Changes
+
+- Add `updatePi()` to `cli/commands/update/root.go`, following the same
+  skip-if-not-installed pattern as `updateClaude`/`updateDevbox`: log and skip when `pi` is
+  not resolvable on `PATH`, otherwise run `pi update` (self-update only, matching the
+  existing narrow scope of each per-tool update step).
+- Call `updatePi()` from `Run()`'s update sequence.
+
+## Impact
+
+- Affected specs: `config-update`
+- Affected code: `cli/commands/update/root.go`
diff --git a/openspec/changes/archive/2026-09-25-add-pi-self-update/specs/config-update/spec.md b/openspec/changes/archive/2026-09-25-add-pi-self-update/specs/config-update/spec.md
new file mode 100644
index 00000000..54818103
--- /dev/null
+++ b/openspec/changes/archive/2026-09-25-add-pi-self-update/specs/config-update/spec.md
@@ -0,0 +1,42 @@
+## MODIFIED Requirements
+
+### Requirement: Update Orchestration
+
+`dots update` SHALL update the environment in sequence: pull and reinstall the
+dots repository (`git fetch`, `git reset --hard origin/master`, `go install
+./...`), update ZSH plugins via zinit (pruning broken completion symlinks),
+update tmux plugins, update Homebrew and outdated packages, update Claude Code,
+Devbox, pi.dev, and the solargraph gem, reshim asdf, and reinstall the `vim`
+component. It SHALL set the tmux window title to `update` while running and
+restore it afterward.
+
+#### Scenario: Dots repo pulled and rebuilt
+
+- **WHEN** `dots update` runs
+- **THEN** it fetches and hard-resets the dots repo to `origin/master` and runs `go install ./...`
+
+#### Scenario: Vim component reinstalled
+
+- **WHEN** `dots update` runs
+- **THEN** it invokes the `vim` installer as part of the update sequence
+
+#### Scenario: pi.dev updated
+
+- **WHEN** `dots update` runs and `pi` is on `PATH`
+- **THEN** it runs `pi update` to self-update the pi.dev binary
+
+### Requirement: Conditional Tool Updates
+
+`dots update` SHALL skip updating Claude Code, Devbox, and pi.dev when their
+commands are not resolvable on `PATH`, logging that they are not installed
+rather than failing.
+
+#### Scenario: Missing tool skipped
+
+- **WHEN** `dots update` runs and `devbox` is not on `PATH`
+- **THEN** the Devbox update is skipped with an informational log and the update continues
+
+#### Scenario: Missing pi.dev skipped
+
+- **WHEN** `dots update` runs and `pi` is not on `PATH`
+- **THEN** the pi.dev update is skipped with an informational log and the update continues
diff --git a/openspec/changes/archive/2026-09-25-add-pi-self-update/tasks.md b/openspec/changes/archive/2026-09-25-add-pi-self-update/tasks.md
new file mode 100644
index 00000000..1d29e813
--- /dev/null
+++ b/openspec/changes/archive/2026-09-25-add-pi-self-update/tasks.md
@@ -0,0 +1,6 @@
+## 1. Implementation
+
+- [x] 1.1 Add `updatePi()` to `cli/commands/update/root.go`: skip with an informational log when `which pi` fails, otherwise run `pi update` via `run.Verbose`
+- [x] 1.2 Call `updatePi()` from `Run()`'s update sequence, alongside `updateClaude()`/`updateDevbox()`
+- [x] 1.3 Update `README.md`'s `pi` component description if it documents install-only behavior (not needed — `dots update`'s per-tool steps aren't enumerated in README)
+- [x] 1.4 Run `go install ./...`, `revive -set_exit_status ./...`, `go test ./...`, `bash .github/skill-tests/run_all.sh`, `bash .github/lint-skills.sh`, `qlty check --all --no-fix --level=high`, `qlty smells --all --no-snippets`
diff --git a/openspec/specs/config-update/spec.md b/openspec/specs/config-update/spec.md
index 979b8fcd..a0b5e3e2 100644
--- a/openspec/specs/config-update/spec.md
+++ b/openspec/specs/config-update/spec.md
@@ -17,9 +17,9 @@ This spec documents the behavior that ships today.
 dots repository (`git fetch`, `git reset --hard origin/master`, `go install
 ./...`), update ZSH plugins via zinit (pruning broken completion symlinks),
 update tmux plugins, update Homebrew and outdated packages, update Claude Code,
-Devbox, and the solargraph gem, reshim asdf, and reinstall the `vim` component.
-It SHALL set the tmux window title to `update` while running and restore it
-afterward.
+Devbox, pi.dev, and the solargraph gem, reshim asdf, and reinstall the `vim`
+component. It SHALL set the tmux window title to `update` while running and
+restore it afterward.
 
 #### Scenario: Dots repo pulled and rebuilt
 
@@ -31,6 +31,11 @@ afterward.
 - **WHEN** `dots update` runs
 - **THEN** it invokes the `vim` installer as part of the update sequence
 
+#### Scenario: pi.dev updated
+
+- **WHEN** `dots update` runs and `pi` is on `PATH`
+- **THEN** it runs `pi update` to self-update the pi.dev binary
+
 ### Requirement: Weekly Auto-Clean
 
 `dots update` SHALL run the cleanup routine before updating only when the
@@ -49,14 +54,20 @@ Within a week of the last clean, the cleanup step SHALL be skipped.
 
 ### Requirement: Conditional Tool Updates
 
-`dots update` SHALL skip updating Claude Code and Devbox when their commands are
-not resolvable on `PATH`, logging that they are not installed rather than failing.
+`dots update` SHALL skip updating Claude Code, Devbox, and pi.dev when their
+commands are not resolvable on `PATH`, logging that they are not installed
+rather than failing.
 
 #### Scenario: Missing tool skipped
 
 - **WHEN** `dots update` runs and `devbox` is not on `PATH`
 - **THEN** the Devbox update is skipped with an informational log and the update continues
 
+#### Scenario: Missing pi.dev skipped
+
+- **WHEN** `dots update` runs and `pi` is not on `PATH`
+- **THEN** the pi.dev update is skipped with an informational log and the update continues
+
 ### Requirement: Cleanup Command
 
 `dots clean` SHALL clean legacy artifacts: `brew cleanup -s` for Homebrew and