diff --git a/scripts/dev_server.py b/scripts/dev_server.py
new file mode 100644
index 00000000..0c8db970
--- /dev/null
+++ b/scripts/dev_server.py
@@ -0,0 +1,169 @@
+#!/usr/bin/env python3
+"""Timmy Time — Development server launcher.
+
+Satisfies tox -e dev criteria:
+  - Graceful port selection (finds next free port if default is taken)
+  - Clickable links to dashboard and other web GUIs
+  - Status line: backend inference source, version, git commit, smoke tests
+  - Auto-reload on code changes (delegates to uvicorn --reload)
+
+Usage: python scripts/dev_server.py [--port PORT]
+"""
+
+import argparse
+import datetime
+import os
+import socket
+import subprocess
+import sys
+
+DEFAULT_PORT = 8000
+MAX_PORT_ATTEMPTS = 10
+OLLAMA_DEFAULT = "http://localhost:11434"
+
+
+def _port_free(port: int) -> bool:
+    """Return True if the TCP port is available on localhost."""
+    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+        try:
+            s.bind(("0.0.0.0", port))
+            return True
+        except OSError:
+            return False
+
+
+def _find_port(start: int) -> int:
+    """Return *start* if free, otherwise probe up to MAX_PORT_ATTEMPTS higher."""
+    for offset in range(MAX_PORT_ATTEMPTS):
+        candidate = start + offset
+        if _port_free(candidate):
+            return candidate
+    raise RuntimeError(
+        f"No free port found in range {start}–{start + MAX_PORT_ATTEMPTS - 1}"
+    )
+
+
+def _git_info() -> str:
+    """Return short commit hash + timestamp, or 'unknown'."""
+    try:
+        sha = subprocess.check_output(
+            ["git", "rev-parse", "--short", "HEAD"],
+            stderr=subprocess.DEVNULL,
+            text=True,
+        ).strip()
+        ts = subprocess.check_output(
+            ["git", "log", "-1", "--format=%ci"],
+            stderr=subprocess.DEVNULL,
+            text=True,
+        ).strip()
+        return f"{sha} ({ts})"
+    except Exception:
+        return "unknown"
+
+
+def _project_version() -> str:
+    """Read version from pyproject.toml without importing toml libs."""
+    pyproject = os.path.join(os.path.dirname(__file__), "..", "pyproject.toml")
+    try:
+        with open(pyproject) as f:
+            for line in f:
+                if line.strip().startswith("version"):
+                    # version = "1.0.0"
+                    return line.split("=", 1)[1].strip().strip('"').strip("'")
+    except Exception:
+        pass
+    return "unknown"
+
+
+def _ollama_url() -> str:
+    return os.environ.get("OLLAMA_URL", OLLAMA_DEFAULT)
+
+
+def _smoke_ollama(url: str) -> str:
+    """Quick connectivity check against Ollama."""
+    import urllib.request
+    import urllib.error
+
+    try:
+        req = urllib.request.Request(url, method="GET")
+        with urllib.request.urlopen(req, timeout=3):
+            return "ok"
+    except Exception:
+        return "unreachable"
+
+
+def _print_banner(port: int) -> None:
+    version = _project_version()
+    git = _git_info()
+    ollama_url = _ollama_url()
+    ollama_status = _smoke_ollama(ollama_url)
+
+    hr = "─" * 62
+    print(flush=True)
+    print(f"  {hr}")
+    print(f"  ┃  Timmy Time — Development Server")
+    print(f"  {hr}")
+    print()
+    print(f"  Dashboard:   http://localhost:{port}")
+    print(f"  API docs:    http://localhost:{port}/docs")
+    print(f"  Health:      http://localhost:{port}/health")
+    print()
+    print(f"  ── Status ──────────────────────────────────────────────")
+    print(f"  Backend:     {ollama_url}  [{ollama_status}]")
+    print(f"  Version:     {version}")
+    print(f"  Git commit:  {git}")
+    print(f"  {hr}")
+    print(flush=True)
+
+
+def main() -> None:
+    parser = argparse.ArgumentParser(description="Timmy dev server")
+    parser.add_argument(
+        "--port",
+        type=int,
+        default=DEFAULT_PORT,
+        help=f"Preferred port (default: {DEFAULT_PORT})",
+    )
+    args = parser.parse_args()
+
+    port = _find_port(args.port)
+    if port != args.port:
+        print(f"  ⚠  Port {args.port} in use — using {port} instead")
+
+    _print_banner(port)
+
+    # Set PYTHONPATH so `timmy` CLI inside the tox venv resolves to this source.
+    src_dir = os.path.join(os.path.dirname(__file__), "..", "src")
+    os.environ["PYTHONPATH"] = os.path.abspath(src_dir)
+
+    # Launch uvicorn with auto-reload
+    cmd = [
+        sys.executable,
+        "-m",
+        "uvicorn",
+        "dashboard.app:app",
+        "--reload",
+        "--host",
+        "0.0.0.0",
+        "--port",
+        str(port),
+        "--reload-dir",
+        os.path.abspath(src_dir),
+        "--reload-include",
+        "*.html",
+        "--reload-include",
+        "*.css",
+        "--reload-include",
+        "*.js",
+        "--reload-exclude",
+        ".claude",
+    ]
+
+    try:
+        subprocess.run(cmd, check=True)
+    except KeyboardInterrupt:
+        print("\n  Shutting down dev server.")
+
+
+if __name__ == "__main__":
+    main()
diff --git a/tox.ini b/tox.ini
index 6626fd87..0be8d624 100644
--- a/tox.ini
+++ b/tox.ini
@@ -163,9 +163,11 @@ commands =
 
 [testenv:dev]
 description = Start dashboard with auto-reload (local development)
+setenv =
+    {[testenv]setenv}
+    TIMMY_TEST_MODE = 0
 commands =
-    uvicorn dashboard.app:app --reload --host 0.0.0.0 --port 8000 \
-        --reload-exclude ".claude"
+    python {toxinidir}/scripts/dev_server.py {posargs}
 
 # ── All Tests (parallel) ─────────────────────────────────────────────────────