diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3672a05b4..e49de62b0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,7 @@
 ## [Unreleased]
 
 - Improved the error message shown when pip install fails due to pip rejecting a package with invalid version metadata. ([#1718](https://github.com/heroku/heroku-buildpack-python/pull/1718))
+- Improved the error message shown when the copy of pip bundled in the `ensurepip` module cannot be found. ([#1720](https://github.com/heroku/heroku-buildpack-python/pull/1720))
 
 ## [v270] - 2024-12-10
 
diff --git a/lib/pip.sh b/lib/pip.sh
index 3b26250f6..c6bedb92a 100644
--- a/lib/pip.sh
+++ b/lib/pip.sh
@@ -15,7 +15,7 @@ function pip::install_pip_setuptools_wheel() {
 	# We use the pip wheel bundled within Python's standard library to install our chosen
 	# pip version, since it's faster than `ensurepip` followed by an upgrade in place.
 	local bundled_pip_module_path
-	bundled_pip_module_path="$(utils::bundled_pip_module_path "${python_home}")"
+	bundled_pip_module_path="$(utils::bundled_pip_module_path "${python_home}" "${python_major_version}")"
 
 	meta_set "pip_version" "${PIP_VERSION}"
 
diff --git a/lib/utils.sh b/lib/utils.sh
index 61254de5c..2bcae44c2 100644
--- a/lib/utils.sh
+++ b/lib/utils.sh
@@ -20,24 +20,31 @@ function utils::get_requirement_version() {
 # pip version from PyPI, saving us from having to download the usual pip bootstrap script.
 function utils::bundled_pip_module_path() {
 	local python_home="${1}"
+	local python_major_version="${2}"
 
-	# We have to use a glob since the bundled wheel filename contains the pip version, which
-	# differs between Python versions. We also have to handle the case where there are multiple
-	# matching pip wheels, since in some versions of Python (eg 3.9.0) multiple versions of pip
-	# were accidentally bundled upstream. Note: This implementation relies upon `nullglob` being
-	# set, which is the case thanks to the `bin/utils` that was run earlier.
-	local bundled_pip_wheel_list=("${python_home}"/lib/python*/ensurepip/_bundled/pip-*.whl)
-	local bundled_pip_wheel="${bundled_pip_wheel_list[0]}"
-
-	if [[ -z "${bundled_pip_wheel}" ]]; then
-		output::error <<-'EOF'
-			Internal Error: Unable to locate the ensurepip pip wheel file.
+	local bundled_wheels_dir="${python_home}/lib/python${python_major_version}/ensurepip/_bundled"
+
+	# We have to use a glob since the bundled wheel filename contains the pip version, which differs
+	# between Python versions. We use compgen to avoid having to set nullglob, since there may be no
+	# matches in the case of a broken Python install. We also have to handle the case where there are
+	# multiple matching pip wheels, since in some versions of Python (eg 3.9.0) multiple versions of
+	# pip were accidentally bundled upstream (we use tail since we want the newest pip version).
+	if bundled_pip_wheel="$(compgen -G "${bundled_wheels_dir}/pip-*.whl" | tail --lines=1)"; then
+		# The pip module exists inside the pip wheel (which is a zip file), however, Python can load
+		# it directly by appending the module name to the zip filename, as though it were a path.
+		echo "${bundled_pip_wheel}/pip"
+	else
+		output::error <<-EOF
+			Internal Error: Unable to locate the bundled copy of pip.
+
+			The Python buildpack could not locate the copy of pip bundled
+			inside Python's 'ensurepip' module:
+
+			$(find "${bundled_wheels_dir}/" 2>&1 || find "${python_home}/" -type d 2>&1 || true)
 		EOF
 		meta_set "failure_reason" "bundled-pip-not-found"
 		exit 1
 	fi
-
-	echo "${bundled_pip_wheel}/pip"
 }
 
 function utils::abort_internal_error() {
diff --git a/spec/fixtures/python_in_app_source/.heroku/python/bin/python b/spec/fixtures/python_in_app_source/.heroku/python/bin/python
new file mode 100644
index 000000000..04b03ed28
--- /dev/null
+++ b/spec/fixtures/python_in_app_source/.heroku/python/bin/python
@@ -0,0 +1,8 @@
+#!/usr/bin/env bash
+
+# This file emulates a Python install having been committed to the app's Git repo.
+# For example, by downloading a slug, extracting it, and committing the results.
+
+set -euo pipefail
+
+exit 0
diff --git a/spec/fixtures/python_in_app_source/.python-version b/spec/fixtures/python_in_app_source/.python-version
new file mode 100644
index 000000000..24ee5b1be
--- /dev/null
+++ b/spec/fixtures/python_in_app_source/.python-version
@@ -0,0 +1 @@
+3.13
diff --git a/spec/fixtures/python_in_app_source/requirements.txt b/spec/fixtures/python_in_app_source/requirements.txt
new file mode 100644
index 000000000..e69de29bb
diff --git a/spec/hatchet/checks_spec.rb b/spec/hatchet/checks_spec.rb
new file mode 100644
index 000000000..d29554821
--- /dev/null
+++ b/spec/hatchet/checks_spec.rb
@@ -0,0 +1,30 @@
+# frozen_string_literal: true
+
+require_relative '../spec_helper'
+
+RSpec.describe 'Buildpack validation checks' do
+  context 'when the app source contains a broken Python install' do
+    let(:app) { Hatchet::Runner.new('spec/fixtures/python_in_app_source', allow_failure: true) }
+
+    it 'fails detection' do
+      app.deploy do |app|
+        expect(clean_output(app.output)).to include(<<~OUTPUT)
+          remote: -----> Python app detected
+          remote: -----> Using Python #{DEFAULT_PYTHON_MAJOR_VERSION} specified in .python-version
+          remote: -----> Using cached install of Python #{DEFAULT_PYTHON_FULL_VERSION}
+          remote: 
+          remote:  !     Internal Error: Unable to locate the bundled copy of pip.
+          remote:  !     
+          remote:  !     The Python buildpack could not locate the copy of pip bundled
+          remote:  !     inside Python's 'ensurepip' module:
+          remote:  !     
+          remote:  !     find: ‘/app/.heroku/python/lib/python3.13/ensurepip/_bundled/’: No such file or directory
+          remote:  !     /app/.heroku/python/
+          remote:  !     /app/.heroku/python/bin
+          remote: 
+          remote:  !     Push rejected, failed to compile Python app.
+        OUTPUT
+      end
+    end
+  end
+end