diff --git a/src/codealmanac/services/updates/models.py b/src/codealmanac/services/updates/models.py
index ab6f68ec..aef3c336 100644
--- a/src/codealmanac/services/updates/models.py
+++ b/src/codealmanac/services/updates/models.py
@@ -12,6 +12,7 @@
 
 class UpdateInstallMethod(StrEnum):
     UV_TOOL = "uv-tool"
+    PIPX = "pipx"
     PIP = "pip"
     EDITABLE = "editable"
     UNKNOWN = "unknown"
diff --git a/src/codealmanac/services/updates/service.py b/src/codealmanac/services/updates/service.py
index 4cb714b4..b41c7c94 100644
--- a/src/codealmanac/services/updates/service.py
+++ b/src/codealmanac/services/updates/service.py
@@ -134,6 +134,9 @@ def plan_update(metadata: PackageInstallMetadata) -> UpdatePlan:
     if method == UpdateInstallMethod.UV_TOOL:
         command = ("uv", "tool", "upgrade", PACKAGE_NAME)
         return runnable_plan(metadata, method, command)
+    if method == UpdateInstallMethod.PIPX:
+        command = ("pipx", "upgrade", PACKAGE_NAME)
+        return runnable_plan(metadata, method, command)
     if method == UpdateInstallMethod.PIP:
         command = (
             str(metadata.python_executable),
@@ -179,9 +182,19 @@ def runnable_plan(
 def update_method(metadata: PackageInstallMetadata) -> UpdateInstallMethod:
     if metadata.editable:
         return UpdateInstallMethod.EDITABLE
+    if is_pipx_install(metadata):
+        return UpdateInstallMethod.PIPX
     installer = (metadata.installer or "").strip().casefold()
     if installer == "uv":
         return UpdateInstallMethod.UV_TOOL
     if installer == "pip":
         return UpdateInstallMethod.PIP
     return UpdateInstallMethod.UNKNOWN
+
+
+def is_pipx_install(metadata: PackageInstallMetadata) -> bool:
+    installer = (metadata.installer or "").strip().casefold()
+    if installer == "pipx":
+        return True
+    parts = tuple(part.casefold() for part in metadata.python_executable.parts)
+    return "pipx" in parts and "venvs" in parts
diff --git a/tests/test_update_service.py b/tests/test_update_service.py
index 10e4b134..81df5748 100644
--- a/tests/test_update_service.py
+++ b/tests/test_update_service.py
@@ -84,6 +84,40 @@ def test_update_service_plans_pip_upgrade_with_current_python():
     )
 
 
+def test_update_service_plans_pipx_upgrade_for_pipx_metadata():
+    service = update_service(
+        PackageInstallMetadata(
+            version="0.1.0",
+            installer="pipx",
+            python_executable=Path("/Users/me/.local/pipx/venvs/codealmanac/bin/python"),
+        ),
+    )
+
+    plan = service.check(CheckUpdateRequest())
+
+    assert plan.status == UpdateStatus.READY
+    assert plan.method == UpdateInstallMethod.PIPX
+    assert plan.command == ("pipx", "upgrade", "codealmanac")
+
+
+def test_update_service_detects_pipx_venv_when_installer_reports_pip():
+    service = update_service(
+        PackageInstallMetadata(
+            version="0.1.0",
+            installer="pip",
+            python_executable=Path(
+                "/Users/me/.local/pipx/venvs/codealmanac/bin/python"
+            ),
+        ),
+    )
+
+    plan = service.check(CheckUpdateRequest())
+
+    assert plan.status == UpdateStatus.READY
+    assert plan.method == UpdateInstallMethod.PIPX
+    assert plan.command == ("pipx", "upgrade", "codealmanac")
+
+
 def test_update_service_refuses_editable_install_without_running_command():
     runner = FakeCommandRunner(PackageCommandResult(exit_code=0))
     service = update_service_with_runner(