diff --git a/.github/workflows/test-cron.yaml b/.github/workflows/test-cron.yaml
index b8221acc701..64760cca9c4 100644
--- a/.github/workflows/test-cron.yaml
+++ b/.github/workflows/test-cron.yaml
@@ -155,9 +155,9 @@ jobs:
       PANTS_REMOTE_CACHE_READ: 'false'
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: github.repository_owner == 'pantsbuild'
-    name: Bootstrap Pants, test Rust (macOS10-x86_64)
+    name: Bootstrap Pants, test Rust (macOS11-x86_64)
     runs-on:
-    - macos-10.15
+    - macos-11
     steps:
     - name: Check out code
       uses: actions/checkout@v3
@@ -195,7 +195,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v3
       with:
-        key: macOS10-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
+        key: macOS11-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
         path: '~/.rustup/toolchains/1.62.1-*
 
           ~/.rustup/update-hashes
@@ -206,7 +206,7 @@ jobs:
     - name: Cache Cargo
       uses: actions/cache@v3
       with:
-        key: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
+        key: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
           }-v1
 
           '
@@ -215,7 +215,7 @@ jobs:
           ~/.cargo/git
 
           '
-        restore-keys: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
+        restore-keys: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
 
           '
     - id: get-engine-hash
@@ -227,7 +227,7 @@ jobs:
     - name: Cache native engine
       uses: actions/cache@v3
       with:
-        key: 'macOS10-x86_64-engine-${ steps.get-engine-hash.outputs.hash }-v1
+        key: 'macOS11-x86_64-engine-${ steps.get-engine-hash.outputs.hash }-v1
 
           '
         path: '.pants
@@ -261,12 +261,12 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v3
       with:
-        name: pants-log-bootstrap-macOS10-x86_64
+        name: pants-log-bootstrap-macOS11-x86_64
         path: .pants.d/pants.log
     - name: Upload native binaries
       uses: actions/upload-artifact@v3
       with:
-        name: native_binaries.${ matrix.python-version }.macOS10-x86_64
+        name: native_binaries.${ matrix.python-version }.macOS11-x86_64
         path: '.pants
 
           src/python/pants/engine/internals/native_engine.so
@@ -777,10 +777,10 @@ jobs:
     env:
       ARCHFLAGS: -arch x86_64
     if: github.repository_owner == 'pantsbuild'
-    name: Test Python (macOS10-x86_64)
+    name: Test Python (macOS11-x86_64)
     needs: bootstrap_pants_macos_x86_64
     runs-on:
-    - macos-10.15
+    - macos-11
     steps:
     - name: Check out code
       uses: actions/checkout@v3
@@ -825,7 +825,7 @@ jobs:
     - name: Download native binaries
       uses: actions/download-artifact@v3
       with:
-        name: native_binaries.${ matrix.python-version }.macOS10-x86_64
+        name: native_binaries.${ matrix.python-version }.macOS11-x86_64
     - if: github.event_name != 'pull_request'
       name: Setup toolchain auth
       run: 'echo TOOLCHAIN_AUTH_TOKEN="${{ secrets.TOOLCHAIN_AUTH_TOKEN }}" >> $GITHUB_ENV
@@ -838,7 +838,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v3
       with:
-        name: pants-log-python-test-macOS10-x86_64
+        name: pants-log-python-test-macOS11-x86_64
         path: .pants.d/pants.log
     strategy:
       matrix:
diff --git a/.github/workflows/test.yaml b/.github/workflows/test.yaml
index 94e23a4c00c..fc06ef02fad 100644
--- a/.github/workflows/test.yaml
+++ b/.github/workflows/test.yaml
@@ -159,12 +159,12 @@ jobs:
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: (github.repository_owner == 'pantsbuild') && (needs.docs_only_check.outputs.docs_only
       != 'DOCS_ONLY')
-    name: Bootstrap Pants, test Rust (macOS10-x86_64)
+    name: Bootstrap Pants, test Rust (macOS11-x86_64)
     needs:
     - check_labels
     - docs_only_check
     runs-on:
-    - macos-10.15
+    - macos-11
     steps:
     - name: Check out code
       uses: actions/checkout@v3
@@ -202,7 +202,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v3
       with:
-        key: macOS10-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
+        key: macOS11-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
         path: '~/.rustup/toolchains/1.62.1-*
 
           ~/.rustup/update-hashes
@@ -213,7 +213,7 @@ jobs:
     - name: Cache Cargo
       uses: actions/cache@v3
       with:
-        key: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
+        key: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
           }-v1
 
           '
@@ -222,7 +222,7 @@ jobs:
           ~/.cargo/git
 
           '
-        restore-keys: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
+        restore-keys: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
 
           '
     - id: get-engine-hash
@@ -234,7 +234,7 @@ jobs:
     - name: Cache native engine
       uses: actions/cache@v3
       with:
-        key: 'macOS10-x86_64-engine-${ steps.get-engine-hash.outputs.hash }-v1
+        key: 'macOS11-x86_64-engine-${ steps.get-engine-hash.outputs.hash }-v1
 
           '
         path: '.pants
@@ -268,12 +268,12 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v3
       with:
-        name: pants-log-bootstrap-macOS10-x86_64
+        name: pants-log-bootstrap-macOS11-x86_64
         path: .pants.d/pants.log
     - name: Upload native binaries
       uses: actions/upload-artifact@v3
       with:
-        name: native_binaries.${ matrix.python-version }.macOS10-x86_64
+        name: native_binaries.${ matrix.python-version }.macOS11-x86_64
         path: '.pants
 
           src/python/pants/engine/internals/native_engine.so
@@ -525,12 +525,12 @@ jobs:
       PANTS_REMOTE_CACHE_WRITE: 'false'
     if: (github.repository_owner == 'pantsbuild') && (needs.docs_only_check.outputs.docs_only
       != 'DOCS_ONLY')
-    name: Build wheels and fs_util (macOS10-x86_64)
+    name: Build wheels and fs_util (macOS11-x86_64)
     needs:
     - check_labels
     - docs_only_check
     runs-on:
-    - macos-10.15
+    - macos-11
     steps:
     - name: Check out code
       uses: actions/checkout@v3
@@ -564,7 +564,7 @@ jobs:
     - name: Cache Rust toolchain
       uses: actions/cache@v3
       with:
-        key: macOS10-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
+        key: macOS11-x86_64-rustup-${ hashFiles('rust-toolchain') }-v1
         path: '~/.rustup/toolchains/1.62.1-*
 
           ~/.rustup/update-hashes
@@ -575,7 +575,7 @@ jobs:
     - name: Cache Cargo
       uses: actions/cache@v3
       with:
-        key: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
+        key: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-${ hashFiles(''src/rust/engine/Cargo.*'')
           }-v1
 
           '
@@ -584,7 +584,7 @@ jobs:
           ~/.cargo/git
 
           '
-        restore-keys: 'macOS10-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
+        restore-keys: 'macOS11-x86_64-cargo-${ hashFiles(''rust-toolchain'') }-
 
           '
     - env:
@@ -614,7 +614,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v3
       with:
-        name: pants-log-wheels-macOS10-x86_64
+        name: pants-log-wheels-macOS11-x86_64
         path: .pants.d/pants.log
     - env:
         AWS_ACCESS_KEY_ID: ${{ secrets.AWS_ACCESS_KEY_ID }}
@@ -1063,13 +1063,13 @@ jobs:
       ARCHFLAGS: -arch x86_64
     if: (github.repository_owner == 'pantsbuild') && (needs.docs_only_check.outputs.docs_only
       != 'DOCS_ONLY')
-    name: Test Python (macOS10-x86_64)
+    name: Test Python (macOS11-x86_64)
     needs:
     - bootstrap_pants_macos_x86_64
     - check_labels
     - docs_only_check
     runs-on:
-    - macos-10.15
+    - macos-11
     steps:
     - name: Check out code
       uses: actions/checkout@v3
@@ -1114,7 +1114,7 @@ jobs:
     - name: Download native binaries
       uses: actions/download-artifact@v3
       with:
-        name: native_binaries.${ matrix.python-version }.macOS10-x86_64
+        name: native_binaries.${ matrix.python-version }.macOS11-x86_64
     - if: github.event_name != 'pull_request'
       name: Setup toolchain auth
       run: 'echo TOOLCHAIN_AUTH_TOKEN="${{ secrets.TOOLCHAIN_AUTH_TOKEN }}" >> $GITHUB_ENV
@@ -1127,7 +1127,7 @@ jobs:
       name: Upload pants.log
       uses: actions/upload-artifact@v3
       with:
-        name: pants-log-python-test-macOS10-x86_64
+        name: pants-log-python-test-macOS11-x86_64
         path: .pants.d/pants.log
     strategy:
       matrix:
diff --git a/build-support/bin/generate_github_workflows.py b/build-support/bin/generate_github_workflows.py
index 65caaf99245..14ba6ef5bed 100644
--- a/build-support/bin/generate_github_workflows.py
+++ b/build-support/bin/generate_github_workflows.py
@@ -33,7 +33,7 @@
 
 class Platform(Enum):
     LINUX_X86_64 = "Linux-x86_64"
-    MACOS10_X86_64 = "macOS10-x86_64"
+    MACOS11_X86_64 = "macOS11-x86_64"
     MACOS11_ARM64 = "macOS11-ARM64"
 
 
@@ -333,8 +333,8 @@ def platform_name(self) -> str:
         return str(self.platform.value)
 
     def runs_on(self) -> list[str]:
-        if self.platform == Platform.MACOS10_X86_64:
-            return ["macos-10.15"]
+        if self.platform == Platform.MACOS11_X86_64:
+            return ["macos-11"]
         if self.platform == Platform.MACOS11_ARM64:
             return ["self-hosted", "macOS11", "ARM64"]
         if self.platform == Platform.LINUX_X86_64:
@@ -343,7 +343,7 @@ def runs_on(self) -> list[str]:
 
     def platform_env(self):
         ret = {}
-        if self.platform == Platform.MACOS10_X86_64:
+        if self.platform == Platform.MACOS11_X86_64:
             # Works around bad `-arch arm64` flag embedded in Xcode 12.x Python interpreters on
             # intel machines. See: https://github.com/giampaolo/psutil/issues/1832
             ret["ARCHFLAGS"] = "-arch x86_64"
@@ -594,7 +594,7 @@ def test_python_linux(shard: str) -> dict[str, Any]:
 
 
 def macos_x86_64_jobs(python_versions: list[str], *, cron: bool) -> Jobs:
-    helper = Helper(Platform.MACOS10_X86_64)
+    helper = Helper(Platform.MACOS11_X86_64)
     jobs = {
         "bootstrap_pants_macos_x86_64": {
             "name": f"Bootstrap Pants, test Rust ({helper.platform_name()})",