diff --git a/.github/workflows/update-nautobot.yml b/.github/workflows/update-nautobot.yml
new file mode 100644
index 000000000..eefa3c782
--- /dev/null
+++ b/.github/workflows/update-nautobot.yml
@@ -0,0 +1,64 @@
+---
+name: "Update Nautobot Version"
+
+on:
+  schedule:
+    # Run every Tuesday at midnight UTC
+    - cron: "0 0 * * 2"
+  workflow_dispatch:
+
+permissions:
+  contents: "write"
+  pull-requests: "write"
+
+jobs:
+  update-nautobot:
+    runs-on: "ubuntu-latest"
+    steps:
+      - name: "Check out repository"
+        uses: "actions/checkout@v4"
+
+      - name: "Set up Python"
+        uses: "actions/setup-python@v5"
+        with:
+          python-version: "3.12"
+
+      - name: "Install Poetry"
+        uses: "snok/install-poetry@v1"
+        with:
+          version: "2.1.3"
+          virtualenvs-create: true
+          virtualenvs-in-project: true
+
+      - name: "Install dependencies"
+        run: "poetry install"
+
+      - name: "Update pyproject.toml with latest Nautobot from PyPI"
+        id: "update"
+        run: "poetry run invoke update-nautobot-deps --output='$GITHUB_OUTPUT'"
+
+      - name: "Update poetry.lock"
+        run: "poetry lock"
+
+      - name: "Create Pull Request"
+        uses: "peter-evans/create-pull-request@v6"
+        with:
+          token: "${{ secrets.GITHUB_TOKEN }}"
+          branch: "deps/nautobot-version-update"
+          delete-branch: true
+          title: "chore: update Nautobot to ${{ steps.update.outputs.version }}"
+          body: |
+            ## Automated Nautobot Version Update
+
+            This PR updates the project to use the latest Nautobot version from PyPI.
+
+            **Changes:**
+            - **nautobot**: `${{ steps.update.outputs.version }}`
+            - **python**: `${{ steps.update.outputs.requires_python }}` (matches Nautobot's requires_python)
+
+            ---
+            *This pull request was created automatically by the [Update Nautobot Version](.github/workflows/update-nautobot.yml) workflow.*
+          labels: |
+            dependencies
+            automated
+          commit-message: "chore: update Nautobot to ${{ steps.update.outputs.version }}"
diff --git a/tasks.py b/tasks.py
index 0114018ab..b0baf797a 100644
--- a/tasks.py
+++ b/tasks.py
@@ -1,7 +1,11 @@
 """Development Tasks."""
 
-from time import sleep
+import json
 import os
+import re
+from time import sleep
+from urllib.request import urlopen
+
 import toml
 from invoke import Collection, task as invoke_task
 
@@ -290,3 +294,93 @@ def db_import(context):
 
     print("Importing DB...\n")
     docker_compose(context, import_cmd, pty=True)
+
+
+# ------------------------------------------------------------------------------
+# NAUTOBOT VERSION UPDATE (for CI / pyproject.toml sync with PyPI)
+# ------------------------------------------------------------------------------
+PYPI_NAUTOBOT_URL = "https://pypi.org/pypi/nautobot/json"
+
+
+def _fetch_nautobot_metadata():
+    """Fetch latest Nautobot version and requires_python from PyPI."""
+    with urlopen(PYPI_NAUTOBOT_URL) as response:
+        data = json.load(response)
+    info = data.get("info", {})
+    version = info.get("version", "")
+    requires_python = info.get("requires_python") or ""
+    if requires_python:
+        # Normalize: PyPI may use '<3.14,>=3.10' or '>=3.10,<3.14'
+        parts = sorted(
+            requires_python.split(","),
+            key=lambda x: (x.strip().startswith("<"), x),
+        )
+        requires_python = ",".join(p.strip() for p in parts)
+    return version, requires_python
+
+
+def _update_pyproject_nautobot(version, requires_python, pyproject_path="pyproject.toml"):
+    """Update nautobot and python version in pyproject.toml."""
+    with open(pyproject_path, "r", encoding="utf-8") as f:
+        content = f.read()
+
+    content = re.sub(
+        r'^(nautobot\s*=\s*)"[^"]*"',
+        rf'\1"{version}"',
+        content,
+        flags=re.MULTILINE,
+    )
+    if requires_python:
+        content = re.sub(
+            r'^(python\s*=\s*)"[^"]*"',
+            rf'\1"{requires_python}"',
+            content,
+            flags=re.MULTILINE,
+        )
+
+    with open(pyproject_path, "w", encoding="utf-8") as f:
+        f.write(content)
+
+
+@task
+def get_latest_nautobot(context):
+    """Fetch and print the latest Nautobot version and requires_python from PyPI."""
+    version, requires_python = _fetch_nautobot_metadata()
+    print(f"Latest Nautobot: {version}, Requires-Python: {requires_python}")
+    return version, requires_python
+
+
+@task(
+    help={
+        "version": "Nautobot version to set (default: fetch from PyPI)",
+        "requires_python": "Python version constraint (default: fetch from PyPI)",
+        "output": "If set (e.g. $GITHUB_OUTPUT), append version= and requires_python= for CI",
+    }
+)
+def update_nautobot_deps(
+    context,
+    version=None,
+    requires_python=None,
+    output=None,
+):
+    """
+    Update pyproject.toml with the latest Nautobot version and Python constraint from PyPI.
+
+    Fetches metadata from PyPI if version/requires_python not provided.
+    Use --output=$GITHUB_OUTPUT in CI to write values for workflow outputs.
+    """
+    if version is None or requires_python is None:
+        fetched_version, fetched_rp = _fetch_nautobot_metadata()
+        version = version or fetched_version
+        requires_python = requires_python or fetched_rp
+
+    _update_pyproject_nautobot(version, requires_python)
+
+    print(f"Updated nautobot to {version}")
+    if requires_python:
+        print(f"Updated python to {requires_python}")
+
+    if output:
+        with open(output, "a", encoding="utf-8") as f:
+            f.write(f"version={version}\n")
+            f.write(f"requires_python={requires_python}\n")