From d392ef8da9415a4e2e715a094e72f238f01df8b5 Mon Sep 17 00:00:00 2001
From: sushi30 <imri.paran@gmail.com>
Date: Sun, 8 Mar 2026 19:17:01 +0100
Subject: [PATCH] feat(docker): add persistent bootstrap script for
 agent-managed capabilities

Add workspace/bootstrap.sh, a script that runs on every container start,
allowing the agent (or user) to persist tool installations across restarts
without rebuilding the image. Errors are logged to bootstrap.error.log and
surfaced in the agent's system prompt so it can self-diagnose and fix the
script.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 docker/entrypoint.sh   | 16 ++++++++++++++++
 pkg/agent/context.go   |  6 ++++++
 workspace/bootstrap.sh | 10 ++++++++++
 3 files changed, 32 insertions(+)
 create mode 100644 workspace/bootstrap.sh

diff --git a/docker/entrypoint.sh b/docker/entrypoint.sh
index b6fc724b5..238af6a1b 100644
--- a/docker/entrypoint.sh
+++ b/docker/entrypoint.sh
@@ -12,4 +12,20 @@ if [ ! -d "${HOME}/.picoclaw/workspace" ] && [ ! -f "${HOME}/.picoclaw/config.js
     exit 0
 fi
 
+# Run bootstrap on every start
+BOOTSTRAP="${HOME}/.picoclaw/workspace/bootstrap.sh"
+ERROR_LOG="${HOME}/.picoclaw/workspace/bootstrap.error.log"
+
+if [ -f "$BOOTSTRAP" ]; then
+    echo "[bootstrap] Running bootstrap.sh..."
+    if sh "$BOOTSTRAP" 2>"$ERROR_LOG"; then
+        # Success — clear any previous error log
+        rm -f "$ERROR_LOG"
+    else
+        echo "[bootstrap] WARNING: bootstrap.sh failed. See $ERROR_LOG for details."
+        echo "[bootstrap] Some capabilities may be missing. The agent will attempt to fix bootstrap.sh."
+        # Do NOT exit — continue starting the gateway so the agent can be reached
+    fi
+fi
+
 exec picoclaw gateway "$@"
diff --git a/pkg/agent/context.go b/pkg/agent/context.go
index c2921294b..b1725a51b 100644
--- a/pkg/agent/context.go
+++ b/pkg/agent/context.go
@@ -465,6 +465,12 @@ func (cb *ContextBuilder) LoadBootstrapFiles() string {
 		}
 	}
 
+	// Surface bootstrap errors so the agent can diagnose and fix bootstrap.sh
+	errorLogPath := filepath.Join(cb.workspace, "bootstrap.error.log")
+	if data, err := os.ReadFile(errorLogPath); err == nil && len(data) > 0 {
+		fmt.Fprintf(&sb, "## BOOTSTRAP ERROR WARNING\n\nThe last container start ran `bootstrap.sh` and it FAILED. Some capabilities may be missing. You should read `bootstrap.sh`, identify the issue, fix it, and tell the user to restart the container.\n\nError output:\n```\n%s\n```\n\n", data)
+	}
+
 	return sb.String()
 }
 
diff --git a/workspace/bootstrap.sh b/workspace/bootstrap.sh
new file mode 100644
index 000000000..8856f77bf
--- /dev/null
+++ b/workspace/bootstrap.sh
@@ -0,0 +1,10 @@
+#!/bin/sh
+# bootstrap.sh — runs on every container start.
+# Edit this file to persist capabilities across restarts.
+# The agent will modify this file when you ask it to install tools.
+
+# Example: GitHub CLI (gh)
+if ! command -v gh >/dev/null 2>&1; then
+    echo "[bootstrap] Installing gh CLI..."
+    apk add --no-cache github-cli
+fi