From 86039e66481ccba9957fa3779e5f0a03e6b5b23d Mon Sep 17 00:00:00 2001
From: Richard Si <sichard26@gmail.com>
Date: Sat, 5 Jul 2025 18:46:17 -0400
Subject: [PATCH 1/2] gh-72327: Suggest using system terminal for pip install
 in REPL

Users new to Python packaging often try to use pip from the REPL only to
be met with a confusing SyntaxError. If this happens, guide the user to
use a system terminal instead to invoke pip.

Co-authored-by: Tom Viner <tom@viner.tv>
Co-authored-by: Brian Schubert <brianm.schubert@gmail.com>
---
 Lib/_pyrepl/console.py                            | 15 ++++++++++++++-
 Lib/test/test_pyrepl/test_pyrepl.py               | 11 +++++++++++
 Misc/ACKS                                         |  2 ++
 .../2025-07-07-16-46-55.gh-issue-72327.wLvRuj.rst |  2 ++
 4 files changed, 29 insertions(+), 1 deletion(-)
 create mode 100644 Misc/NEWS.d/next/Library/2025-07-07-16-46-55.gh-issue-72327.wLvRuj.rst

diff --git a/Lib/_pyrepl/console.py b/Lib/_pyrepl/console.py
index 8956fb1242e52a..85f0a7cfd33f15 100644
--- a/Lib/_pyrepl/console.py
+++ b/Lib/_pyrepl/console.py
@@ -27,6 +27,7 @@
 import linecache
 from dataclasses import dataclass, field
 import os.path
+import re
 import sys
 
 
@@ -195,7 +196,19 @@ def runsource(self, source, filename="<input>", symbol="single"):
                 ast.PyCF_ONLY_AST,
                 incomplete_input=False,
             )
-        except (SyntaxError, OverflowError, ValueError):
+        except SyntaxError as e:
+            # If it looks like pip install was entered (a common beginner
+            # mistake), provide a hint to use the system command prompt.
+            if re.match(r"^\s*(py(thon3?)? -m pip|pip3?) install.*", source):
+                e.add_note(
+                    "The Python package manager (pip) can only be used"
+                    " outside of the Python REPL.\n"
+                    "Try the 'pip' command in a separate terminal or"
+                    " command prompt."
+                )
+            self.showsyntaxerror(filename, source=source)
+            return False
+        except (OverflowError, ValueError):
             self.showsyntaxerror(filename, source=source)
             return False
         if tree.body:
diff --git a/Lib/test/test_pyrepl/test_pyrepl.py b/Lib/test/test_pyrepl/test_pyrepl.py
index 98bae7dd703fd9..e7bf39b3995bb3 100644
--- a/Lib/test/test_pyrepl/test_pyrepl.py
+++ b/Lib/test/test_pyrepl/test_pyrepl.py
@@ -1757,3 +1757,14 @@ def test_showrefcount(self):
         output, _ = self.run_repl("1\n1+2\nexit()\n", cmdline_args=['-Xshowrefcount'], env=env)
         matches = re.findall(r'\[-?\d+ refs, \d+ blocks\]', output)
         self.assertEqual(len(matches), 3)
+
+    def test_detect_pip_usage_in_repl(self):
+        for pip_cmd in ("pip", "pip3", "python -m pip", "python3 -m pip"):
+            with self.subTest(pip_cmd=pip_cmd):
+                output, exit_code = self.run_repl([f"{pip_cmd} install antigravity", "exit"])
+                self.assertIn("SyntaxError", output)
+                hint = (
+                    "The Python package manager (pip) can only be used"
+                    " outside of the Python REPL"
+                )
+                self.assertIn(hint, output)
diff --git a/Misc/ACKS b/Misc/ACKS
index d1490e1e46ccfd..aa0bbdec258d47 100644
--- a/Misc/ACKS
+++ b/Misc/ACKS
@@ -1742,6 +1742,7 @@ Joel Shprentz
 Yue Shuaijie
 Jaysinh Shukla
 Terrel Shumway
+Richard Si
 Eric Siegerman
 Reilly Tucker Siemens
 Paul Sijben
@@ -1986,6 +1987,7 @@ Olivier Vielpeau
 Kannan Vijayan
 Kurt Vile
 Norman Vine
+Tom Viner
 Pauli Virtanen
 Frank Visser
 Long Vo
diff --git a/Misc/NEWS.d/next/Library/2025-07-07-16-46-55.gh-issue-72327.wLvRuj.rst b/Misc/NEWS.d/next/Library/2025-07-07-16-46-55.gh-issue-72327.wLvRuj.rst
new file mode 100644
index 00000000000000..f305abb655a6f6
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2025-07-07-16-46-55.gh-issue-72327.wLvRuj.rst
@@ -0,0 +1,2 @@
+Suggest using the system command prompt when ``pip install`` is typed into
+the REPL. Patch by Tom Viner, Richard Si, and Brian Schubert.

From 187542af0a215f46a200550932e5d0adbd8af670 Mon Sep 17 00:00:00 2001
From: Richard Si <sichard26@gmail.com>
Date: Fri, 11 Jul 2025 10:17:48 -0400
Subject: [PATCH 2/2] Update Lib/test/test_pyrepl/test_pyrepl.py

Co-authored-by: Hugo van Kemenade <1324225+hugovk@users.noreply.github.com>
---
 Lib/test/test_pyrepl/test_pyrepl.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/Lib/test/test_pyrepl/test_pyrepl.py b/Lib/test/test_pyrepl/test_pyrepl.py
index e7bf39b3995bb3..657a971f8769df 100644
--- a/Lib/test/test_pyrepl/test_pyrepl.py
+++ b/Lib/test/test_pyrepl/test_pyrepl.py
@@ -1761,7 +1761,7 @@ def test_showrefcount(self):
     def test_detect_pip_usage_in_repl(self):
         for pip_cmd in ("pip", "pip3", "python -m pip", "python3 -m pip"):
             with self.subTest(pip_cmd=pip_cmd):
-                output, exit_code = self.run_repl([f"{pip_cmd} install antigravity", "exit"])
+                output, exit_code = self.run_repl([f"{pip_cmd} install sampleproject", "exit"])
                 self.assertIn("SyntaxError", output)
                 hint = (
                     "The Python package manager (pip) can only be used"

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