diff --git a/scripts/dev_server.sh b/scripts/dev_server.sh
new file mode 100755
index 00000000..f22326d8
--- /dev/null
+++ b/scripts/dev_server.sh
@@ -0,0 +1,191 @@
+#!/usr/bin/env bash
+# ── Timmy Time — Development Environment Launcher ────────────────────────────
+#
+# Starts the full dev stack via docker compose with:
+#   • Auto port selection (finds a free port starting at 8000)
+#   • Clickable dashboard + service links
+#   • Status line (version, git commit, backend inference)
+#   • Smoke test on startup
+#   • Drops into a dev shell with `timmy` CLI wired to this instance
+#
+# Usage:
+#   tox -e dev
+#   # or directly: bash scripts/dev_server.sh
+set -euo pipefail
+
+REPO_ROOT="$(cd "$(dirname "$0")/.." && pwd)"
+cd "$REPO_ROOT"
+
+# ── Colours ──────────────────────────────────────────────────────────────────
+GREEN='\033[0;32m'  AMBER='\033[0;33m'  RED='\033[0;31m'
+CYAN='\033[0;36m'   BOLD='\033[1m'      DIM='\033[2m'
+RESET='\033[0m'
+
+# ── Find a free port ─────────────────────────────────────────────────────────
+find_free_port() {
+    local port="${1:-8000}"
+    local max_port=$((port + 20))
+    while [ "$port" -le "$max_port" ]; do
+        if ! lsof -iTCP:"$port" -sTCP:LISTEN >/dev/null 2>&1; then
+            echo "$port"
+            return 0
+        fi
+        echo -e "${DIM}  port $port in use, trying next...${RESET}" >&2
+        port=$((port + 1))
+    done
+    echo -e "${RED}ERROR: No free port found in range 8000-$max_port${RESET}" >&2
+    return 1
+}
+
+PORT=$(find_free_port 8000)
+
+# ── Gather version info ─────────────────────────────────────────────────────
+VERSION=$(python3 -c "
+try:
+    import tomllib
+except ImportError:
+    import tomli as tomllib
+with open('pyproject.toml', 'rb') as f:
+    print(tomllib.load(f)['tool']['poetry']['version'])
+" 2>/dev/null || echo "unknown")
+
+GIT_COMMIT=$(git rev-parse --short HEAD 2>/dev/null || echo "unknown")
+GIT_TIMESTAMP=$(git log -1 --format='%ci' 2>/dev/null || echo "unknown")
+GIT_BRANCH=$(git branch --show-current 2>/dev/null || echo "unknown")
+
+# ── Detect backend inference source ──────────────────────────────────────────
+OLLAMA_URL="${OLLAMA_URL:-http://localhost:11434}"
+INFERENCE_SOURCE="Ollama @ ${OLLAMA_URL}"
+if curl -sf "${OLLAMA_URL}/api/tags" >/dev/null 2>&1; then
+    OLLAMA_STATUS="${GREEN}reachable${RESET}"
+else
+    OLLAMA_STATUS="${AMBER}unreachable${RESET}"
+fi
+
+# ── Banner ───────────────────────────────────────────────────────────────────
+echo ""
+echo -e "${BOLD}${CYAN}╔══════════════════════════════════════════════════════════════╗${RESET}"
+echo -e "${BOLD}${CYAN}║          TIMMY TIME — Development Environment               ║${RESET}"
+echo -e "${BOLD}${CYAN}╚══════════════════════════════════════════════════════════════╝${RESET}"
+echo ""
+
+# ── Status line ──────────────────────────────────────────────────────────────
+echo -e "${BOLD}Status${RESET}"
+echo -e "  Version:    ${GREEN}v${VERSION}${RESET} ${DIM}(${GIT_BRANCH} @ ${GIT_COMMIT})${RESET}"
+echo -e "  Commit:     ${DIM}${GIT_TIMESTAMP}${RESET}"
+echo -e "  Inference:  ${INFERENCE_SOURCE} [${OLLAMA_STATUS}]"
+echo ""
+
+# ── Start docker compose ────────────────────────────────────────────────────
+echo -e "${BOLD}Starting services...${RESET}"
+export TIMMY_DEV_PORT="$PORT"
+
+# Ensure data directory exists for volume mount
+mkdir -p "$REPO_ROOT/data"
+
+docker compose \
+    -f docker-compose.yml \
+    -f docker-compose.dev.yml \
+    -p "timmy-dev" \
+    up -d --build \
+    --remove-orphans 2>&1 | tail -5
+
+# Override the published port via env
+docker compose \
+    -f docker-compose.yml \
+    -f docker-compose.dev.yml \
+    -p "timmy-dev" \
+    port dashboard 8000 >/dev/null 2>&1 || true
+
+# If the port override didn't work via compose, stop and re-create with the right port
+# We use a dev-specific override to set the port dynamically
+if [ "$PORT" != "8000" ]; then
+    echo -e "${DIM}  Rebinding to port $PORT...${RESET}"
+    docker compose -p "timmy-dev" down --remove-orphans >/dev/null 2>&1 || true
+
+    # Create a temporary override for the port
+    OVERRIDE_FILE=$(mktemp /tmp/timmy-dev-port.XXXXXX.yml)
+    cat > "$OVERRIDE_FILE" <<EOF
+services:
+  dashboard:
+    ports:
+      - "${PORT}:8000"
+EOF
+    docker compose \
+        -f docker-compose.yml \
+        -f docker-compose.dev.yml \
+        -f "$OVERRIDE_FILE" \
+        -p "timmy-dev" \
+        up -d --build \
+        --remove-orphans 2>&1 | tail -5
+    rm -f "$OVERRIDE_FILE"
+fi
+
+# ── Wait for healthy ────────────────────────────────────────────────────────
+echo -ne "${DIM}  Waiting for dashboard to become healthy...${RESET}"
+HEALTHY=false
+for i in $(seq 1 30); do
+    if curl -sf "http://localhost:${PORT}/health" >/dev/null 2>&1; then
+        HEALTHY=true
+        break
+    fi
+    echo -n "."
+    sleep 1
+done
+echo ""
+
+# ── Smoke test ───────────────────────────────────────────────────────────────
+echo ""
+echo -e "${BOLD}Smoke Tests${RESET}"
+if [ "$HEALTHY" = true ]; then
+    echo -e "  Dashboard health:  ${GREEN}PASS${RESET}"
+else
+    echo -e "  Dashboard health:  ${RED}FAIL${RESET} ${DIM}(may still be starting)${RESET}"
+fi
+
+# Check Ollama connectivity from inside the container
+if curl -sf "${OLLAMA_URL}/api/tags" >/dev/null 2>&1; then
+    echo -e "  Ollama reachable:  ${GREEN}PASS${RESET}"
+else
+    echo -e "  Ollama reachable:  ${AMBER}SKIP${RESET} ${DIM}(optional service)${RESET}"
+fi
+
+# ── Clickable links ─────────────────────────────────────────────────────────
+echo ""
+echo -e "${BOLD}Services${RESET}"
+echo -e "  Dashboard:   ${CYAN}http://localhost:${PORT}${RESET}"
+echo -e "  Health:      ${CYAN}http://localhost:${PORT}/health${RESET}"
+echo -e "  API docs:    ${CYAN}http://localhost:${PORT}/docs${RESET}"
+echo -e "  Ollama:      ${CYAN}${OLLAMA_URL}${RESET}"
+echo ""
+
+# ── Dev shell ────────────────────────────────────────────────────────────────
+echo -e "${BOLD}Dev Shell${RESET}"
+echo -e "  ${DIM}The \`timmy\` CLI is available and points to this dev instance.${RESET}"
+echo -e "  ${DIM}Type 'exit' or Ctrl-D to stop the dev environment.${RESET}"
+echo ""
+
+cleanup() {
+    echo ""
+    echo -e "${AMBER}Shutting down dev environment...${RESET}"
+    docker compose -p "timmy-dev" down --remove-orphans 2>/dev/null || true
+    echo -e "${GREEN}Dev environment stopped.${RESET}"
+}
+trap cleanup EXIT
+
+# Drop into a subshell with the dev environment on PATH
+export PYTHONPATH="$REPO_ROOT/src:${PYTHONPATH:-}"
+export PATH="$REPO_ROOT/.venv/bin:$PATH"
+export TIMMY_DEV=1
+export OLLAMA_URL
+export PS1="(timmy-dev) \w \$ "
+
+exec bash --norc --noprofile -c "
+    export PS1='${GREEN}(timmy-dev)${RESET} \w \$ '
+    export PYTHONPATH='$PYTHONPATH'
+    export PATH='$PATH'
+    export TIMMY_DEV=1
+    export OLLAMA_URL='$OLLAMA_URL'
+    echo 'Ready. Try: timmy status'
+    exec bash --norc -i
+"
diff --git a/tox.ini b/tox.ini
index 6626fd87..e7be18f9 100644
--- a/tox.ini
+++ b/tox.ini
@@ -162,10 +162,9 @@ commands =
 # ── Dev Server ───────────────────────────────────────────────────────────────
 
 [testenv:dev]
-description = Start dashboard with auto-reload (local development)
+description = Full dev environment — docker compose + auto-reload + dev shell
 commands =
-    uvicorn dashboard.app:app --reload --host 0.0.0.0 --port 8000 \
-        --reload-exclude ".claude"
+    bash scripts/dev_server.sh
 
 # ── All Tests (parallel) ─────────────────────────────────────────────────────