diff --git a/manifest.yml b/manifest.yml
index a8d92b58..8a6b8622 100644
--- a/manifest.yml
+++ b/manifest.yml
@@ -88,21 +88,21 @@ dependencies:
   source: https://files.pythonhosted.org/packages/20/16/650289cd3f43d5a2fadfd98c68bd1e1e7f2550a1a5326768cddfbcedb2c5/pip-25.2.tar.gz
   source_sha256: 578283f006390f85bb6282dffb876454593d637f5d1be494b5202ce4877e71f2
 - name: pip
-  version: 26.2.1
-  uri: https://buildpacks.cloudfoundry.org/dependencies/pip/pip_26.2.1_linux_noarch_cflinuxfs4_22e7a825.tgz
-  sha256: 22e7a8258b20b0f50f713d1e506c228c1ca7620aa3b483b67266b90392eeb91e
+  version: 26.2.2
+  uri: https://buildpacks.cloudfoundry.org/dependencies/pip/pip_26.2.2_linux_noarch_cflinuxfs4_d876df6b.tgz
+  sha256: d876df6b58ea3264950a319c11d4d98e9a4095a774ae9b6d98edec1563a98679
   cf_stacks:
   - cflinuxfs4
-  source: https://files.pythonhosted.org/packages/ae/15/4500e320e6b101ec3b719ae85b697d9940b6cda672bc555bd6016fc60c6f/pip-26.2.1.tar.gz
-  source_sha256: f6ad667e89a1fe78046c8f13232b247200f5258d7828f3f7883d660878e0813f
+  source: https://files.pythonhosted.org/packages/fa/e8/0842d757e483e895e670f655084cfe8b8c72580c6769a76b30b2789a0608/pip-26.2.2.tar.gz
+  source_sha256: 3a8e5c800492787f33a4114ef54444546c340df428974ebba17e0fd47e11af2f
 - name: pip
-  version: 26.2.1
-  uri: https://buildpacks.cloudfoundry.org/dependencies/pip/pip_26.2.1_linux_noarch_cflinuxfs5_22e7a825.tgz
-  sha256: 22e7a8258b20b0f50f713d1e506c228c1ca7620aa3b483b67266b90392eeb91e
+  version: 26.2.2
+  uri: https://buildpacks.cloudfoundry.org/dependencies/pip/pip_26.2.2_linux_noarch_cflinuxfs5_94205d18.tgz
+  sha256: 94205d18befb483e86afe50f75cd7a48a019da986af57d77330c0f446e8f5415
   cf_stacks:
   - cflinuxfs5
-  source: https://files.pythonhosted.org/packages/ae/15/4500e320e6b101ec3b719ae85b697d9940b6cda672bc555bd6016fc60c6f/pip-26.2.1.tar.gz
-  source_sha256: f6ad667e89a1fe78046c8f13232b247200f5258d7828f3f7883d660878e0813f
+  source: https://files.pythonhosted.org/packages/fa/e8/0842d757e483e895e670f655084cfe8b8c72580c6769a76b30b2789a0608/pip-26.2.2.tar.gz
+  source_sha256: 3a8e5c800492787f33a4114ef54444546c340df428974ebba17e0fd47e11af2f
 - name: pipenv
   version: 2024.4.1
   uri: https://buildpacks.cloudfoundry.org/dependencies/pipenv/pipenv_2024.4.1_linux_noarch_cflinuxfs3_b3c74c78.tgz
diff --git a/src/python/supply/supply.go b/src/python/supply/supply.go
index 44cb9499..613c055d 100644
--- a/src/python/supply/supply.go
+++ b/src/python/supply/supply.go
@@ -341,12 +341,35 @@ func (s *Supplier) InstallPip() error {
 		return err
 	}
 
+	// The pip dependency tarball bundles a flit-core wheel (the build backend
+	// required by pip's pyproject.toml). We must bootstrap flit-core into the
+	// Python environment before installing pip, because:
+	//   - pip's pyproject.toml declares build-requires: flit-core >=3.11,<4
+	//   - With build isolation, pip would try to install flit-core into a
+	//     temporary venv, but --no-index prevents network access and the
+	//     bundled flit-core version may not satisfy the <4 constraint
+	//   - With --no-build-isolation, pip skips the isolated env but needs
+	//     flit_core importable in the current environment
+	// This matches the pattern used by InstallCommonBuildDependencies().
+	s.Log.Info("Installing build backend flit-core (bootstrap)")
+	if err := s.Command.Execute(s.Stager.BuildDir(), indentWriter(os.Stdout), indentWriter(os.Stderr),
+		"python",
+		"-m", "pip",
+		"install", "flit-core",
+		"--no-index",
+		"--no-build-isolation",
+		fmt.Sprintf("--find-links=%s", tempPath),
+	); err != nil {
+		return fmt.Errorf("could not bootstrap flit-core: %v", err)
+	}
+
 	if err := s.Command.Execute(s.Stager.BuildDir(), indentWriter(os.Stdout), indentWriter(os.Stderr),
 		"python",
 		"-m", "pip",
 		"install", "pip",
 		"--exists-action=w",
 		"--no-index",
+		"--no-build-isolation",
 		"--ignore-installed",
 		fmt.Sprintf("--find-links=%s", tempPath),
 	); err != nil {
@@ -765,7 +788,6 @@ func (s *Supplier) InstallCommonBuildDependencies() error {
 		}
 	}
 
-
 	return nil
 }
 
diff --git a/src/python/supply/supply_test.go b/src/python/supply/supply_test.go
index a8d15d41..b6533dee 100644
--- a/src/python/supply/supply_test.go
+++ b/src/python/supply/supply_test.go
@@ -154,7 +154,10 @@ var _ = Describe("Supply", func() {
 
 			It("installs latest from manifest", func() {
 				mockInstaller.EXPECT().InstallOnlyVersion("pip", "/tmp/pip")
-				mockCommand.EXPECT().Execute(buildDir, gomock.Any(), gomock.Any(), "python", "-m", "pip", "install", "pip", "--exists-action=w", "--no-index", "--ignore-installed", "--find-links=/tmp/pip")
+				gomock.InOrder(
+					mockCommand.EXPECT().Execute(buildDir, gomock.Any(), gomock.Any(), "python", "-m", "pip", "install", "flit-core", "--no-index", "--no-build-isolation", "--find-links=/tmp/pip"),
+					mockCommand.EXPECT().Execute(buildDir, gomock.Any(), gomock.Any(), "python", "-m", "pip", "install", "pip", "--exists-action=w", "--no-index", "--no-build-isolation", "--ignore-installed", "--find-links=/tmp/pip"),
+				)
 				mockStager.EXPECT().LinkDirectoryInDepDir(filepath.Join(filepath.Join(depDir, "python"), "bin"), "bin")
 
 				Expect(supplier.InstallPip()).To(Succeed())