diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index d8af7f47..787b87b5 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -39,6 +39,20 @@ jobs:
       - name: 🧪 Run tests
         run: "python -m unittest"
 
+  test-typer-compat:
+    runs-on: ubuntu-latest
+    strategy:
+      matrix:
+        typer: ["typer==0.27.2", "typer"]
+    steps:
+      - uses: actions/checkout@v4
+      - uses: actions/setup-python@v5
+        with:
+          python-version: '3.10'
+      - run: pip install --upgrade ".[dev]" "${{ matrix.typer }}"
+      - run: make check_code_quality
+      - run: python -m unittest discover -s tests/cli -t .
+
   test-slim:
     runs-on: ubuntu-latest
     steps:
@@ -58,4 +72,6 @@ jobs:
           pip install -e . --no-deps
           pip install responses
       - name: 🧪 Run slim-compatible tests
-        run: "python -m unittest tests.test_slim_compat tests.test_vision_events"
+        run: >-
+          python -m unittest tests.test_slim_compat tests.test_vision_events
+          tests.cli.test_typer_integration tests.cli.test_completion_handler
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3de8e4fd..35ea8569 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,14 @@ All notable changes to this project will be documented in this file.
 
 ## Unreleased
 
+### Changed
+
+- Migrate CLI error handling to Typer's public exception API, preserving JSON
+  usage errors, aborts, completion failures and argument ordering. Require
+  Typer >=0.27.2 in both full and slim installs and remove the external Click
+  dependency; test the minimum and latest Typer releases. This raises the
+  previous minimum from 0.12.0 to use the supported exception API.
+
 ### Added
 
 - `Project.autolabel(..., keypoint_confidence_threshold=0.75)` and
diff --git a/requirements-slim.txt b/requirements-slim.txt
index 9c4d021e..2c5b03d9 100644
--- a/requirements-slim.txt
+++ b/requirements-slim.txt
@@ -6,8 +6,7 @@ tqdm>=4.41.0
 PyYAML>=5.3.1
 requests_toolbelt
 filetype
-typer>=0.12.0,<0.26  # 0.26 vendors click, dropping the external dep the CLI imports
-click>=8.0
+typer>=0.27.2
 python-dateutil
 python-dotenv
 six
diff --git a/requirements.txt b/requirements.txt
index 2a105758..53c63eb9 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -16,5 +16,4 @@ tqdm>=4.41.0
 PyYAML>=5.3.1
 requests_toolbelt
 filetype
-typer>=0.12.0,<0.26  # 0.26 vendors click, dropping the external dep the CLI imports
-click>=8.0
+typer>=0.27.2
diff --git a/roboflow/cli/__init__.py b/roboflow/cli/__init__.py
index bb52cf56..99f56b51 100644
--- a/roboflow/cli/__init__.py
+++ b/roboflow/cli/__init__.py
@@ -10,7 +10,6 @@
 import os
 from typing import Annotated, Any, Optional
 
-import click
 import typer
 
 import roboflow
@@ -417,15 +416,16 @@ def main() -> None:
             # Exit code 2 = Click usage error (missing arg, bad option)
             # Other codes = our output_error already printed JSON
             raise
-        except click.exceptions.UsageError as exc:
-            # Click/typer validation error — emit JSON on stderr
+        except typer.TyperException as exc:
+            # Use Typer's public exception API, including its usage-error exit code.
             import json as _json
 
-            # format_message() keeps the option name that str() drops for bad values.
-            payload = {"error": {"message": exc.format_message(), "hint": "Run with --help for usage information."}}
+            payload = {"error": {"message": exc.format_message()}}
+            if exc.exit_code == 2:
+                payload["error"]["hint"] = "Run with --help for usage information."
             print(_json.dumps(payload), file=sys.stderr)
-            sys.exit(2)
-        except click.exceptions.Abort:
+            sys.exit(exc.exit_code)
+        except typer.Abort:
             sys.exit(1)
         except Exception as exc:
             import json as _json
diff --git a/roboflow/cli/_compat.py b/roboflow/cli/_compat.py
index ae6b1804..9ca7868b 100644
--- a/roboflow/cli/_compat.py
+++ b/roboflow/cli/_compat.py
@@ -11,11 +11,10 @@
 import types
 from typing import Any
 
-import click
 import typer  # noqa: TC002 — needed at runtime for Context type
 
 
-def _sort_params(params: list[click.Parameter]) -> None:
+def _sort_params(params: list[Any]) -> None:
     """Sort params in-place: required first, then alphabetical by option name."""
     params.sort(
         key=lambda p: (
@@ -24,7 +23,7 @@ def _sort_params(params: list[click.Parameter]) -> None:
             # Required options first
             not getattr(p, "required", False),
             # Arguments before options (positionals first)
-            not isinstance(p, click.Argument),
+            not isinstance(p, typer.core.TyperArgument),
             # Alphabetical by the first long option name
             (p.opts[0].lstrip("-") if hasattr(p, "opts") and p.opts else p.name or ""),
         )
@@ -39,15 +38,15 @@ class SortedGroup(typer.core.TyperGroup):
     required options first).
     """
 
-    def list_commands(self, ctx: click.Context) -> list[str]:  # type: ignore[override]
+    def list_commands(self, ctx: Any) -> list[str]:
         return sorted(super().list_commands(ctx))
 
-    def format_help(self, ctx: click.Context, formatter: click.HelpFormatter) -> None:
+    def format_help(self, ctx: Any, formatter: Any) -> None:
         """Sort options alphabetically before rendering help."""
         _sort_params(self.params)
         super().format_help(ctx, formatter)
 
-    def get_command(self, ctx: click.Context, cmd_name: str) -> click.Command | None:  # type: ignore[override]
+    def get_command(self, ctx: Any, cmd_name: str) -> Any:
         """Wrap returned commands to sort their options too."""
         cmd = super().get_command(ctx, cmd_name)
         if cmd is not None and not isinstance(cmd, SortedGroup):
diff --git a/roboflow/cli/handlers/completion.py b/roboflow/cli/handlers/completion.py
index 8acebd71..24c8cbe4 100644
--- a/roboflow/cli/handlers/completion.py
+++ b/roboflow/cli/handlers/completion.py
@@ -10,7 +10,6 @@
 import shutil
 from typing import Annotated, Optional
 
-import click
 import typer
 from typer._completion_classes import completion_init
 from typer._completion_shared import get_completion_script
@@ -72,7 +71,7 @@ def install(
 
     try:
         installed_shell, path = typer_install(shell=shell, prog_name="roboflow", complete_var="_ROBOFLOW_COMPLETE")
-    except click.exceptions.Exit:
+    except typer.Exit:
         output_error(
             args,
             "Could not detect or install completion.",
diff --git a/tests/cli/test_completion_handler.py b/tests/cli/test_completion_handler.py
index d701543e..70cc00b0 100644
--- a/tests/cli/test_completion_handler.py
+++ b/tests/cli/test_completion_handler.py
@@ -12,7 +12,6 @@
 from pathlib import Path
 from unittest import mock
 
-import click
 from typer.testing import CliRunner
 
 from roboflow.cli import app
@@ -78,7 +77,7 @@ def test_hidden_commands_filtered_from_completion(self) -> None:
         from roboflow.cli import app as rf_app
 
         click_app = typer.main.get_command(rf_app)
-        ctx = click.Context(click_app, info_name="roboflow")
+        ctx = click_app.make_context("roboflow", [], resilient_parsing=True)
         visible = {
             name
             for name in click_app.list_commands(ctx)
diff --git a/tests/cli/test_typer_integration.py b/tests/cli/test_typer_integration.py
new file mode 100644
index 00000000..fb0d4463
--- /dev/null
+++ b/tests/cli/test_typer_integration.py
@@ -0,0 +1,69 @@
+import io
+import json
+import sys
+import unittest
+from contextlib import redirect_stderr
+from unittest.mock import patch
+
+import typer
+
+from roboflow.cli import main
+from roboflow.cli._compat import _sort_params
+
+
+class TestTyperIntegration(unittest.TestCase):
+    def test_json_usage_errors(self):
+        cases = (
+            (["project", "get"], "Missing argument"),
+            (["--bad-option"], "--bad-option"),
+            (["image", "search", "example", "--limit", "not-an-int"], "--limit"),
+        )
+        for args, message in cases:
+            with self.subTest(args=args):
+                stderr = io.StringIO()
+                with patch.object(sys, "argv", ["roboflow", "--json", *args]):
+                    with redirect_stderr(stderr), self.assertRaises(SystemExit) as error:
+                        main()
+                self.assertEqual(error.exception.code, 2)
+                payload = json.loads(stderr.getvalue())
+                self.assertIn("hint", payload["error"])
+                self.assertIn(message, payload["error"]["message"])
+
+    def test_json_abort(self):
+        with patch.object(sys, "argv", ["roboflow", "--json"]):
+            with patch("roboflow.cli.app", side_effect=typer.Abort):
+                stderr = io.StringIO()
+                with redirect_stderr(stderr), self.assertRaises(SystemExit) as error:
+                    main()
+        self.assertEqual(error.exception.code, 1)
+        # Preserve the existing silent cancellation behavior.
+        self.assertEqual(stderr.getvalue(), "")
+
+    def test_json_application_error_keeps_its_exit_code(self):
+        for exit_code in (1, 7):
+            with self.subTest(exit_code=exit_code):
+                exception = typer.TyperException("Request failed")
+                exception.exit_code = exit_code
+                with patch.object(sys, "argv", ["roboflow", "--json"]):
+                    with patch("roboflow.cli.app", side_effect=exception):
+                        stderr = io.StringIO()
+                        with redirect_stderr(stderr), self.assertRaises(SystemExit) as error:
+                            main()
+                self.assertEqual(error.exception.code, exit_code)
+                self.assertEqual(json.loads(stderr.getvalue()), {"error": {"message": "Request failed"}})
+
+    def test_json_non_typer_error_remains_generic(self):
+        with patch.object(sys, "argv", ["roboflow", "--json"]):
+            with patch("roboflow.cli.app", side_effect=ValueError("Unexpected failure")):
+                stderr = io.StringIO()
+                with redirect_stderr(stderr), self.assertRaises(SystemExit) as error:
+                    main()
+        self.assertEqual(error.exception.code, 1)
+        self.assertEqual(json.loads(stderr.getvalue()), {"error": {"message": "Unexpected failure"}})
+
+    def test_arguments_sort_before_required_options(self):
+        argument = typer.core.TyperArgument(param_decls=["zulu"], required=True)
+        option = typer.core.TyperOption(param_decls=["--alpha"], required=True)
+        params = [option, argument]
+        _sort_params(params)
+        self.assertEqual(params, [argument, option])