diff --git a/README.md b/README.md
index f85a097..adf7d9d 100644
--- a/README.md
+++ b/README.md
@@ -151,8 +151,8 @@ Shipkit is a layered content system for Claude Code. Skills and guidelines flow
 ## Quick Start
 
 ```bash
-# 1. Install shipkit
-pip install shipkit
+# 1. Install shipkit (uv recommended, pip also works)
+uv tool install shipkit  # or: pip install shipkit
 
 # 2. Run the interactive installer
 shipkit install
diff --git a/shipkit/cli.py b/shipkit/cli.py
index 881f082..386df47 100644
--- a/shipkit/cli.py
+++ b/shipkit/cli.py
@@ -275,7 +275,7 @@ def uninstall(yes: bool):
     click.echo()
     click.echo("✅ Shipkit uninstalled successfully.")
     click.echo()
-    click.echo("To reinstall later: pip install shipkit && shipkit install")
+    click.echo("To reinstall later: uv tool install shipkit && shipkit install")
 
 
 @main.command()
diff --git a/shipkit/core/hooks/update_check.py b/shipkit/core/hooks/update_check.py
index ab1b772..a942aca 100644
--- a/shipkit/core/hooks/update_check.py
+++ b/shipkit/core/hooks/update_check.py
@@ -78,7 +78,7 @@ def _output_update_message(latest: str, current: str) -> None:
     """Print the update notification for agent context injection."""
     print(f"INSTRUCTION: shipkit {latest} is available (current: {current}). "
           f'Mention once at a natural pause: "💡 By the way: There\'s a new shipkit version ({latest}) available. '
-          f"Run /update-shipkit or pip install --upgrade shipkit to update.\" "
+          f"Run /update-shipkit to update.\" "
           f"Then don't mention it again this session.")
 
 
diff --git a/shipkit/core/skills/update-shipkit/SKILL.md b/shipkit/core/skills/update-shipkit/SKILL.md
index 1e070b1..696cd9b 100644
--- a/shipkit/core/skills/update-shipkit/SKILL.md
+++ b/shipkit/core/skills/update-shipkit/SKILL.md
@@ -1,6 +1,6 @@
 ---
 name: update-shipkit
-description: Update shipkit to the latest version from PyPI. Handles pip upgrade and core content refresh. Use when update notification appears or user wants latest features.
+description: Update shipkit to the latest version from PyPI. Handles uv/pip upgrade and core content refresh. Use when update notification appears or user wants latest features.
 ---
 
 # Update Shipkit Skill
@@ -9,7 +9,7 @@ Automated shipkit upgrade workflow.
 
 ## When To Use
 
-- When you see: "💡 There's a new shipkit version available"
+- When you see: "There's a new shipkit version available"
 - When user says: "update shipkit", "upgrade shipkit", "get latest shipkit"
 - Periodically to stay current with new features
 
@@ -21,15 +21,32 @@ Automated shipkit upgrade workflow.
 shipkit --version
 ```
 
-### Step 2: Check Available Version on PyPI
+### Step 2: Detect Installation Method
+
+Determine how shipkit was installed so we use the right upgrade command:
+
+```bash
+# Check if installed via uv tool
+uv tool list 2>/dev/null | grep shipkit
+
+# Check if installed in a uv-managed environment
+pip show shipkit 2>/dev/null | grep Location
+```
+
+- If `uv tool list` shows shipkit: it's a **uv tool install**
+- If location is inside a `.venv`: it's a **uv/pip project install**
+- Otherwise: it's a **regular pip install**
+
+### Step 3: Check Available Version on PyPI
 
 ```bash
-pip index versions shipkit
+# Prefer uv if available
+uv pip index versions shipkit 2>/dev/null || pip index versions shipkit
 ```
 
-Compare current vs available.
+Compare current vs available. If already on latest, tell user and stop.
 
-### Step 3: Confirm Upgrade
+### Step 4: Confirm Upgrade
 
 Show user:
 ```
@@ -42,23 +59,36 @@ New in 0.1.5:
 Would you like to upgrade?
 ```
 
-### Step 4: Upgrade
+### Step 5: Upgrade
+
+Use the method matching the installation:
+
+**uv tool install (recommended):**
+```bash
+uv tool upgrade shipkit
+```
+
+**uv pip (project venv):**
+```bash
+uv pip install --upgrade shipkit
+```
 
+**pip fallback:**
 ```bash
 pip install --upgrade shipkit
 ```
 
-### Step 5: Refresh Core Content
+### Step 6: Refresh Core Content
 
-After pip upgrade, refresh core content in ~/.config/shipkit/:
+After upgrading the package, refresh core content in ~/.config/shipkit/:
 
 ```bash
 shipkit upgrade
 ```
 
-This copies latest core/experimental/advanced from pip package to user space.
+This copies latest core/experimental/advanced from the updated package to user space and recreates symlinks.
 
-### Step 6: Verify
+### Step 7: Verify
 
 ```bash
 shipkit --version
@@ -66,11 +96,11 @@ shipkit --version
 
 Should show new version.
 
-### Step 7: Next Steps
+### Step 8: Next Steps
 
 Tell user:
 ```
-✅ Shipkit upgraded: 0.1.2 → 0.1.5
+Shipkit upgraded: 0.1.2 -> 0.1.5
 
 Changes take effect:
 - New skills: Available immediately (already symlinked)
@@ -83,17 +113,18 @@ Restart Claude Code to activate new hooks.
 ## Error Handling
 
 **"No newer version available"**
-→ "Already on latest version (0.1.5)"
+-> "Already on latest version (0.1.5)"
 
-**"pip upgrade failed"**
-→ Show error, suggest: pip install --upgrade --force-reinstall shipkit
+**"Upgrade failed"**
+-> Show error, suggest: `uv pip install --upgrade --force-reinstall shipkit` or `pip install --upgrade --force-reinstall shipkit`
 
 **"shipkit upgrade failed"**
-→ Show error, may need manual cleanup
+-> Show error, may need manual cleanup of ~/.config/shipkit/
 
 ## Key Principles
 
+- Detect installation method before upgrading (uv tool vs uv pip vs pip)
 - Always show what's changing (version numbers)
-- Run shipkit upgrade after pip (refreshes core)
+- Run `shipkit upgrade` after package upgrade (refreshes core content)
 - Remind to restart Claude (hooks)
 - Test that upgrade worked (verify version)
diff --git a/shipkit/core/skills/update/SKILL.md b/shipkit/core/skills/update/SKILL.md
index 9de915e..e6f5b0e 100644
--- a/shipkit/core/skills/update/SKILL.md
+++ b/shipkit/core/skills/update/SKILL.md
@@ -18,7 +18,9 @@ Find the shipkit installation and determine the update path.
 - Run `python -c "import shipkit; import pathlib; print(pathlib.Path(shipkit.__file__).parent.parent)"` to find the package root
 - Check if it's a git repo: look for `.git/` in the package root
 - If git clone: update via git (proceed to step 2)
-- If installed via uv/pip: tell user to run `uv pip install --upgrade shipkit` or `uv sync --upgrade-package shipkit`, then skip to step 5
+- If installed via uv tool: update with `uv tool upgrade shipkit`, then skip to step 5
+- If installed via uv/pip in a venv: update with `uv pip install --upgrade shipkit`, then skip to step 5
+- If installed via pip: update with `pip install --upgrade shipkit`, then skip to step 5
 - Check for uncommitted local changes to the shipkit repo and warn
 
 ### 2. Check for Updates