diff --git a/.claude/hooks/session-start.sh b/.claude/hooks/session-start.sh
new file mode 100755
index 0000000..750d168
--- /dev/null
+++ b/.claude/hooks/session-start.sh
@@ -0,0 +1,48 @@
+#!/bin/bash
+# .claude/hooks/session-start.sh
+# Session-start hook for Claude Code on the web.
+# Installs AIWB runtime and dev dependencies (bats, shellcheck, fzf, gum).
+# Idempotent — safe to re-run on session resume/clear.
+
+set -euo pipefail
+
+# Only run in remote Claude Code sessions
+if [ "${CLAUDE_CODE_REMOTE:-}" != "true" ]; then
+  exit 0
+fi
+
+# ── Charm apt repo (needed for gum) ──────────────────────────────────────────
+if ! command -v gum >/dev/null 2>&1; then
+  echo "==> Adding Charm apt repo for gum..."
+  mkdir -p /etc/apt/keyrings
+  curl -fsSL https://repo.charm.sh/apt/gpg.key \
+    | gpg --dearmor -o /etc/apt/keyrings/charm.gpg
+  echo "deb [signed-by=/etc/apt/keyrings/charm.gpg] https://repo.charm.sh/apt/ * *" \
+    > /etc/apt/sources.list.d/charm.list
+fi
+
+# ── Determine which packages actually need installing ─────────────────────────
+MISSING=()
+command -v bats       >/dev/null 2>&1 || MISSING+=(bats)
+command -v shellcheck >/dev/null 2>&1 || MISSING+=(shellcheck)
+command -v fzf        >/dev/null 2>&1 || MISSING+=(fzf)
+command -v gum        >/dev/null 2>&1 || MISSING+=(gum)
+
+if [ ${#MISSING[@]} -eq 0 ]; then
+  echo "==> All AIWB dependencies already installed."
+  exit 0
+fi
+
+echo "==> Installing missing packages: ${MISSING[*]}"
+apt-get update -qq
+DEBIAN_FRONTEND=noninteractive apt-get install -y --no-install-recommends \
+  "${MISSING[@]}"
+
+# ── Verify ────────────────────────────────────────────────────────────────────
+echo "==> Verifying installed tools:"
+bats       --version
+shellcheck --version | head -1
+fzf        --version
+gum        --version
+
+echo "==> AIWB session-start hook complete."
diff --git a/.claude/settings.json b/.claude/settings.json
index 5c150e9..5125148 100644
--- a/.claude/settings.json
+++ b/.claude/settings.json
@@ -5,5 +5,17 @@
     "scripts/**",
     "examples/**",
     "templates/**"
-  ]
+  ],
+  "hooks": {
+    "SessionStart": [
+      {
+        "hooks": [
+          {
+            "type": "command",
+            "command": "$CLAUDE_PROJECT_DIR/.claude/hooks/session-start.sh"
+          }
+        ]
+      }
+    ]
+  }
 }