diff --git a/.devcontainer/Dockerfile b/.devcontainer/Dockerfile
index be7a2eb57798..5d43a035f300 100644
--- a/.devcontainer/Dockerfile
+++ b/.devcontainer/Dockerfile
@@ -6,7 +6,7 @@ RUN version=1.42.1 \
     && golangci-lint version
 
 # Install pulumictl
-RUN version=0.0.25 \
+RUN version=0.0.42 \
     && curl -fsSLO https://github.com/pulumi/pulumictl/releases/download/v$version/pulumictl-v$version-linux-amd64.tar.gz \
     && tar -xzf pulumictl-v$version-linux-amd64.tar.gz --directory /usr/local/bin --no-same-owner pulumictl \
     && rm -f pulumictl-v$version-linux-amd64.tar.gz \
diff --git a/.github/workflows/ci-run-test.yml b/.github/workflows/ci-run-test.yml
index 1847a1e22f1b..b1cfd74f8262 100644
--- a/.github/workflows/ci-run-test.yml
+++ b/.github/workflows/ci-run-test.yml
@@ -203,7 +203,7 @@ jobs:
           GITHUB_TOKEN: ${{ secrets.PULUMI_BOT_TOKEN }}
         with:
           repo: pulumi/pulumictl
-          tag: v0.0.32
+          tag: v0.0.42
           cache: enable
       - name: Install gotestsum
         uses: jaxxstorm/action-install-gh-release@v1.7.1
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index bd0e4e1dbccd..35eca9862548 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -175,7 +175,7 @@ jobs:
           GITHUB_TOKEN: ${{ secrets.PULUMI_BOT_TOKEN }}
         with:
           repo: pulumi/pulumictl
-          tag: v0.0.32
+          tag: v0.0.42
           cache: enable
       - name: Repository Dispatch
         run: ${{ matrix.job.run-command }}
diff --git a/.gitpod/Dockerfile b/.gitpod/Dockerfile
index f5156620bcd0..bd8061e31ea5 100644
--- a/.gitpod/Dockerfile
+++ b/.gitpod/Dockerfile
@@ -8,7 +8,7 @@ ENV PATH="$HOME/.pulumi:$HOME/.pulumi/bin:$PATH"
 RUN mkdir -p /home/gitpod/dotnet && \
      curl -fsSL https://download.visualstudio.microsoft.com/download/pr/f65a8eb0-4537-4e69-8ff3-1a80a80d9341/cc0ca9ff8b9634f3d9780ec5915c1c66/dotnet-sdk-3.1.201-linux-x64.tar.gz \
      | tar xz -C /home/gitpod/dotnet && \
-     wget -qO- https://github.com/pulumi/pulumictl/releases/download/v0.0.28/pulumictl-v0.0.28-linux-amd64.tar.gz | sudo tar zxvf - -C /usr/local/bin
+     wget -qO- https://github.com/pulumi/pulumictl/releases/download/v0.0.42/pulumictl-v0.0.42-linux-amd64.tar.gz | sudo tar zxvf - -C /usr/local/bin
 
 
 ENV DOTNET_ROOT=/home/gitpod/dotnet
diff --git a/tests/integration/integration_python_test.go b/tests/integration/integration_python_test.go
index 34d4ef2cd495..335073a51fb5 100644
--- a/tests/integration/integration_python_test.go
+++ b/tests/integration/integration_python_test.go
@@ -1061,3 +1061,18 @@ func TestConstructProviderPropagationPython(t *testing.T) {
 		filepath.Join("..", "..", "sdk", "python", "env", "src"),
 	})
 }
+
+// Regression test for https://github.com/pulumi/pulumi/issues/9411
+func TestDuplicateOutputPython(t *testing.T) {
+	integration.ProgramTest(t, &integration.ProgramTestOptions{
+		Dir: filepath.Join("python", "duplicate-output"),
+		Dependencies: []string{
+			filepath.Join("..", "..", "sdk", "python", "env", "src"),
+		},
+		ExtraRuntimeValidation: func(t *testing.T, stack integration.RuntimeValidationStackInfo) {
+			expected := []interface{}{float64(1), float64(2)}
+			assert.Equal(t, expected, stack.Outputs["export1"])
+			assert.Equal(t, expected, stack.Outputs["export2"])
+		},
+	})
+}
diff --git a/tests/integration/python/duplicate-output/.gitignore b/tests/integration/python/duplicate-output/.gitignore
new file mode 100644
index 000000000000..28a6abfd4dd0
--- /dev/null
+++ b/tests/integration/python/duplicate-output/.gitignore
@@ -0,0 +1,6 @@
+*.pyc
+/.pulumi/
+/dist/
+/*.egg-info
+venv/
+lib/
diff --git a/tests/integration/python/duplicate-output/Pulumi.yaml b/tests/integration/python/duplicate-output/Pulumi.yaml
new file mode 100644
index 000000000000..70a611b95613
--- /dev/null
+++ b/tests/integration/python/duplicate-output/Pulumi.yaml
@@ -0,0 +1,3 @@
+name: pulumi-python-duplicate-output
+description: A Python program that tests returning the same output twice.
+runtime: python
diff --git a/tests/integration/python/duplicate-output/__main__.py b/tests/integration/python/duplicate-output/__main__.py
new file mode 100644
index 000000000000..bb9c7d299268
--- /dev/null
+++ b/tests/integration/python/duplicate-output/__main__.py
@@ -0,0 +1,8 @@
+# Copyright 2016-2023, Pulumi Corporation.  All rights reserved.
+
+import pulumi
+
+a = pulumi.Output.from_input([1, 2])
+
+pulumi.export("export1", a)
+pulumi.export("export2", a)
\ No newline at end of file
diff --git a/tests/integration/python/duplicate-output/requirements.txt b/tests/integration/python/duplicate-output/requirements.txt
new file mode 100644
index 000000000000..b1dc38733acb
--- /dev/null
+++ b/tests/integration/python/duplicate-output/requirements.txt
@@ -0,0 +1 @@
+pulumi