diff --git a/.github/workflows/create_release.yml b/.github/workflows/create_release.yml
index f2a84af977..07a7508f34 100644
--- a/.github/workflows/create_release.yml
+++ b/.github/workflows/create_release.yml
@@ -464,7 +464,9 @@ jobs:
       - name: Package CLI binary
         run: |
           mv ${{ steps.bundle_cli.outputs.binary_path }} oz-${{ steps.get-config.outputs.channel }}
-          tar czf oz-${{ steps.get-config.outputs.channel }}-macos-${{ matrix.arch }}.tar.gz oz-${{ steps.get-config.outputs.channel }} -C "$(dirname "${{ steps.bundle_cli.outputs.bundled_resources_dir }}")" resources
+          tar czf oz-${{ steps.get-config.outputs.channel }}-macos-${{ matrix.arch }}.tar.gz \
+            oz-${{ steps.get-config.outputs.channel }} \
+            -C "$(dirname "${{ steps.bundle_cli.outputs.bundled_resources_dir }}")" resources lib
 
       - name: Add CLI to GitHub release assets
         if: ${{ needs.prepare_release.outputs.should_publish == 'true' }}
diff --git a/crates/remote_server/src/install_remote_server.sh b/crates/remote_server/src/install_remote_server.sh
index 721ceaca7b..84dca018bc 100644
--- a/crates/remote_server/src/install_remote_server.sh
+++ b/crates/remote_server/src/install_remote_server.sh
@@ -55,6 +55,29 @@ cleanup() {
 }
 trap cleanup EXIT
 
+install_lib_dir() {
+  extracted_lib_dir="$1"
+  staged_lib_dir="$install_dir/.lib.$(basename "$tmpdir")"
+  backup_lib_dir="$install_dir/.lib.previous.$(basename "$tmpdir")"
+
+  rm -rf "$staged_lib_dir" "$backup_lib_dir"
+  mv "$extracted_lib_dir" "$staged_lib_dir"
+
+  if [ -e "$install_dir/lib" ]; then
+    mv "$install_dir/lib" "$backup_lib_dir"
+  fi
+
+  if mv "$staged_lib_dir" "$install_dir/lib"; then
+    rm -rf "$backup_lib_dir"
+  else
+    if [ -e "$backup_lib_dir" ]; then
+      mv "$backup_lib_dir" "$install_dir/lib"
+    fi
+    rm -rf "$staged_lib_dir"
+    exit 1
+  fi
+}
+
 staging_tarball_path="{staging_tarball_path}"
 if [ -n "$staging_tarball_path" ]; then
   # SCP fallback: tarball already uploaded by the client.
@@ -82,4 +105,7 @@ tar -xzf "$tmpdir/oz.tar.gz" -C "$tmpdir"
 bin=$(find "$tmpdir" -type f -name 'oz*' ! -name '*.tar.gz' | head -n1)
 if [ -z "$bin" ]; then echo "no binary found in tarball" >&2; exit 1; fi
 chmod +x "$bin"
+if [ -d "$tmpdir/lib" ]; then
+  install_lib_dir "$tmpdir/lib"
+fi
 mv "$bin" "$install_dir/{binary_name}{version_suffix}"
diff --git a/crates/remote_server/src/setup_tests.rs b/crates/remote_server/src/setup_tests.rs
index e9a238de57..3a806e95a3 100644
--- a/crates/remote_server/src/setup_tests.rs
+++ b/crates/remote_server/src/setup_tests.rs
@@ -366,6 +366,133 @@ fn install_script_avoids_pattern_substitution_for_tilde_expansion() {
     );
 }
 
+/// Regression: macOS CLI tarballs may include Swift runtime libraries
+/// in a `lib/` sidecar next to the standalone binary. The installer
+/// must preserve the binary's existing final path while installing the
+/// sidecar at `$install_dir/lib` using the production shell script.
+#[cfg(unix)]
+#[test]
+fn install_script_installs_lib_sidecar_without_changing_binary_path() {
+    use command::blocking::Command;
+    use std::{
+        fs,
+        io::Write,
+        path::{Path, PathBuf},
+        process::Stdio,
+        time::{SystemTime, UNIX_EPOCH},
+    };
+
+    struct TempDir {
+        path: PathBuf,
+    }
+
+    impl TempDir {
+        fn new() -> Self {
+            let nanos = SystemTime::now()
+                .duration_since(UNIX_EPOCH)
+                .expect("system time should be after UNIX epoch")
+                .as_nanos();
+            let path = std::env::temp_dir().join(format!(
+                "warp-remote-install-lib-sidecar-{}-{nanos}",
+                std::process::id()
+            ));
+            fs::create_dir_all(&path).expect("failed to create temp dir");
+            Self { path }
+        }
+
+        fn path(&self) -> &Path {
+            &self.path
+        }
+    }
+
+    impl Drop for TempDir {
+        fn drop(&mut self) {
+            let _ = fs::remove_dir_all(&self.path);
+        }
+    }
+
+    let temp = TempDir::new();
+    let fake_home = temp.path().join("home");
+    let package_dir = temp.path().join("package");
+    let lib_dir = package_dir.join("lib");
+    fs::create_dir_all(&lib_dir).expect("failed to create package lib dir");
+
+    let binary_path = package_dir.join("oz-test");
+    let mut binary = fs::File::create(&binary_path).expect("failed to create package binary");
+    writeln!(binary, "#!/bin/sh").expect("failed to write package binary");
+    writeln!(binary, "echo test").expect("failed to write package binary");
+
+    fs::write(lib_dir.join("libswiftCore.dylib"), "swift").expect("failed to write dylib");
+
+    let tarball_path = temp.path().join("oz.tar.gz");
+    let tar_output = Command::new("tar")
+        .arg("-czf")
+        .arg(&tarball_path)
+        .arg("-C")
+        .arg(&package_dir)
+        .arg(".")
+        .stdout(Stdio::piped())
+        .stderr(Stdio::piped())
+        .output()
+        .expect("failed to run tar");
+    assert!(
+        tar_output.status.success(),
+        "tar failed with {:?}: stderr={}",
+        tar_output.status,
+        String::from_utf8_lossy(&tar_output.stderr),
+    );
+
+    fs::create_dir_all(&fake_home).expect("failed to create fake home");
+    let script = install_script(Some(
+        tarball_path
+            .to_str()
+            .expect("temp tarball path should be valid UTF-8"),
+    ));
+
+    let bash = if Path::new("/bin/bash").exists() {
+        "/bin/bash"
+    } else {
+        "bash"
+    };
+    let output = Command::new(bash)
+        .arg("-c")
+        .arg(&script)
+        .env("HOME", &fake_home)
+        .stdout(Stdio::piped())
+        .stderr(Stdio::piped())
+        .output()
+        .expect("failed to run install script");
+    assert!(
+        output.status.success(),
+        "install script failed with {:?}: stderr={}",
+        output.status,
+        String::from_utf8_lossy(&output.stderr),
+    );
+
+    let installed_binary = remote_server_binary().replacen(
+        '~',
+        fake_home
+            .to_str()
+            .expect("fake home path should be valid UTF-8"),
+        1,
+    );
+    assert!(
+        Path::new(&installed_binary).is_file(),
+        "expected binary at unchanged remote-server path: {installed_binary}",
+    );
+
+    let installed_lib = remote_server_dir().replacen(
+        '~',
+        fake_home
+            .to_str()
+            .expect("fake home path should be valid UTF-8"),
+        1,
+    ) + "/lib/libswiftCore.dylib";
+    assert!(
+        Path::new(&installed_lib).is_file(),
+        "expected Swift sidecar dylib at {installed_lib}",
+    );
+}
 #[test]
 fn version_hash_is_deterministic() {
     // version_hash uses the compile-time GIT_RELEASE_TAG which is typically
diff --git a/script/macos/bundle b/script/macos/bundle
index 4e87c7daa8..a7a08c2f69 100755
--- a/script/macos/bundle
+++ b/script/macos/bundle
@@ -92,6 +92,53 @@ function relpath() {
   python -c "import os,sys;print(os.path.relpath(*(sys.argv[1:])))" "$@";
 }
 
+function add_rpath_if_missing() {
+  local binary_path="$1"
+  local rpath="$2"
+
+  if otool -l "$binary_path" | awk -v rpath="$rpath" '
+    /LC_RPATH/ { in_rpath = 1; next }
+    in_rpath && $1 == "path" {
+      if ($2 == rpath) { found = 1 }
+      in_rpath = 0
+    }
+    END { exit found ? 0 : 1 }
+  '; then
+    echo "$binary_path already has rpath $rpath"
+  else
+    echo "Adding rpath $rpath to $binary_path"
+    install_name_tool -add_rpath "$rpath" "$binary_path"
+  fi
+}
+
+function copy_swift_stdlibs_for_cli() {
+  local binary_path="$1"
+  local destination="$2"
+  local swift_stdlib_tool_output
+  swift_stdlib_tool_output="$(mktemp -d -t swift-stdlib-tool-XXXXXXXXXX)"
+
+  rm -rf "$destination"
+
+  mkdir -p "$destination"
+  echo "Copying Swift runtime libraries required by $binary_path into $destination"
+  xcrun swift-stdlib-tool \
+    --copy \
+    --scan-executable "$binary_path" \
+    --platform macosx \
+    --destination "$swift_stdlib_tool_output"
+
+  find "$swift_stdlib_tool_output" -type f -name 'libswift*.dylib' -maxdepth 3 -print0 | while IFS= read -r -d '' dylib_path; do
+    cp -p "$dylib_path" "$destination/"
+  done
+  # Do not rewrite /usr/lib/swift load commands to @rpath. Xcode's x86_64
+  # backward-deployment Swift 5.0 dylibs are only valid before macOS 10.14.4
+  # and abort on newer macOS when loaded directly. Keeping the system Swift
+  # load commands preserves modern runtime behavior while still packaging the
+  # stdlibs swift-stdlib-tool reports for the archive layout.
+
+  rm -rf "$swift_stdlib_tool_output"
+}
+
 # Defaults for command-line flags.
 UNIVERSAL_BINARY=true
 BUILD_BINARY=true
@@ -587,6 +634,10 @@ elif [[ "$ARTIFACT" == "cli" ]]; then
 
   echo "Copying binary into $OUT_DIR/$WARP_BIN"
   cp "target/$DEFAULT_TARGET/$TARGET_PROFILE_DIR/$WARP_BIN" "$OUT_DIR/$WARP_BIN"
+  # Prefer system Swift libraries on macOS versions that provide them, and fall
+  # back to the sidecar lib directory on older systems.
+  add_rpath_if_missing "$OUT_DIR/$WARP_BIN" "/usr/lib/swift"
+  add_rpath_if_missing "$OUT_DIR/$WARP_BIN" "@executable_path/lib"
 
   if [[ -n "$TARGET_ARCH" && -e "target/$DEFAULT_TARGET/$TARGET_PROFILE_DIR/$WARP_BIN.dSYM" ]]; then
     echo "Copying .dSYM into $OUT_DIR/$WARP_BIN.dSYM"
@@ -596,6 +647,8 @@ elif [[ "$ARTIFACT" == "cli" ]]; then
   echo "Preparing CLI resources directory"
   BUNDLED_RESOURCES_DIR="$OUT_DIR/resources"
   "$WORKSPACE_ROOT_DIR/script/prepare_bundled_resources" "$BUNDLED_RESOURCES_DIR" "$RELEASE_CHANNEL" "$CARGO_PROFILE"
+  CLI_SWIFT_STDLIB_DIR="$OUT_DIR/lib"
+  copy_swift_stdlibs_for_cli "$OUT_DIR/$WARP_BIN" "$CLI_SWIFT_STDLIB_DIR"
 
 
   # Set the primary binary path to output.
@@ -840,6 +893,10 @@ if [ "${GITHUB_ACTIONS}" == "true" ]; then
   if [[ -n "$BUNDLED_RESOURCES_DIR" ]]; then
     echo "bundled_resources_dir=$BUNDLED_RESOURCES_DIR" >> "$GITHUB_OUTPUT"
   fi
+
+  if [[ -n "$CLI_SWIFT_STDLIB_DIR" ]]; then
+    echo "cli_swift_stdlib_dir=$CLI_SWIFT_STDLIB_DIR" >> "$GITHUB_OUTPUT"
+  fi
   
   echo "::echo::off"
 fi