diff --git a/.github/workflows/release.yaml b/.github/workflows/release.yaml
index f0fec4e2e..b21fe0e33 100644
--- a/.github/workflows/release.yaml
+++ b/.github/workflows/release.yaml
@@ -63,12 +63,18 @@ jobs:
           - target: x86_64-unknown-linux-musl
             os: ubuntu-24.04
             attr: nativelink-x86_64-linux
+            # The runner shares this target's architecture, so the packaged
+            # binary can be executed to prove it actually starts.
+            smoke_test: true
           - target: aarch64-unknown-linux-musl
             os: ubuntu-24.04
             attr: nativelink-aarch64-linux
+            # Cross-built from x86_64, so the runner cannot execute it.
+            smoke_test: false
           - target: aarch64-apple-darwin
             os: macos-26
             attr: nativelink-aarch64-darwin
+            smoke_test: true
     runs-on: ${{ matrix.os }}
     timeout-minutes: 90
     env:
@@ -125,6 +131,38 @@ jobs:
           sha256 "${ASSET}.tar.gz" | tee "${ASSET}.tar.gz.sha256"
           echo "asset=${ASSET}" >> "${GITHUB_OUTPUT}"
 
+      # The v1.6.6 macOS tarball shipped with an absolute /nix/store install
+      # name for libiconv and could not launch on any machine but the builder
+      # (#2727). The Nix build now fails on a leftover store reference, and
+      # this re-checks the packaged tarball so a regression cannot reach a
+      # published release unnoticed.
+      - name: Smoke test packaged binary
+        if: matrix.smoke_test
+        run: |
+          set -euo pipefail
+          ASSET="${{ steps.package.outputs.asset }}"
+          CHECK="$(mktemp -d)"
+          tar -C "${CHECK}" -xzf "${ASSET}.tar.gz"
+
+          if [[ "${{ runner.os }}" == "macOS" ]]; then
+            otool -L "${CHECK}/nativelink"
+            if otool -L "${CHECK}/nativelink" | tail -n +2 | grep '/nix/store'; then
+              echo "::error::Packaged macOS binary links against /nix/store paths that do not exist on user machines."
+              exit 1
+            fi
+            codesign --verify --verbose "${CHECK}/nativelink"
+          fi
+
+          # nativelink exits non-zero with a usage message when handed no
+          # config file. Reaching that message proves dyld loaded the binary
+          # and it ran, which is all this check needs to establish.
+          output="$("${CHECK}/nativelink" 2>&1 || true)"
+          echo "${output}"
+          if ! echo "${output}" | grep -q 'Usage: nativelink'; then
+            echo "::error::Packaged binary for ${{ matrix.target }} did not start."
+            exit 1
+          fi
+
       - name: Generate SBOM
         uses: >- # v0.24.0
           anchore/sbom-action@e22c389904149dbc22b58101806040fa8d37a610
diff --git a/flake.nix b/flake.nix
index 42a15e6c5..0b5f65392 100644
--- a/flake.nix
+++ b/flake.nix
@@ -171,6 +171,60 @@
         cargoArtifactsFor = p: (craneLibFor p).buildDepsOnly (commonArgsFor p);
         nightlyCargoArtifactsFor = p: (nightlyCraneLibFor p).buildDepsOnly (commonArgsFor p);
 
+        # Darwin binaries link against Nix's `libiconv`, which records an
+        # absolute `/nix/store/...` install name. That path only exists on the
+        # machine that built the binary, so the published macOS tarball failed
+        # to launch anywhere else with a dyld "Library not loaded" error.
+        #
+        # Nix's darwin `libiconv` is Apple's own libiconv and exports the same
+        # symbols as the copy macOS keeps in the dyld shared cache, so pointing
+        # the install name at `/usr/lib` is ABI-safe and leaves the binary with
+        # no Nix store references at all.
+        #
+        # See https://github.com/TraceMachina/nativelink/issues/2727.
+        darwinSystemDylibArgs = p: {
+          # `install_name_tool` invalidates the ad-hoc signature that arm64
+          # macOS requires. This hook re-signs during fixup, i.e. after the
+          # `preFixup` rewrite below.
+          nativeBuildInputs =
+            (commonArgsFor p).nativeBuildInputs
+            ++ [p.darwin.autoSignDarwinBinariesHook];
+
+          preFixup = ''
+            for binary in "$out"/bin/*; do
+              [ -f "$binary" ] || continue
+
+              # Skip anything that isn't a Mach-O image, such as wrapper scripts.
+              linkage="$(otool -L "$binary" 2>/dev/null)" || continue
+
+              printf '%s\n' "$linkage" | tail -n +2 | awk '{print $1}' \
+              | while read -r dylib; do
+                case "$dylib" in
+                  /nix/store/*/lib/libiconv*.dylib | /nix/store/*/lib/libcharset*.dylib)
+                    echo "relocating $dylib -> /usr/lib/''${dylib##*/} in $binary"
+                    install_name_tool \
+                      -change "$dylib" "/usr/lib/''${dylib##*/}" "$binary"
+                    ;;
+                esac
+              done
+
+              remaining="$(
+                otool -L "$binary" | tail -n +2 | awk '{print $1}' \
+                | grep '^/nix/store' || true
+              )"
+              if [ -n "$remaining" ]; then
+                echo "error: $binary still links against Nix store libraries:" >&2
+                echo "$remaining" >&2
+                echo "Those paths do not exist on machines without Nix, so the" >&2
+                echo "released binary would fail to launch. Either relocate the" >&2
+                echo "library to its /usr/lib equivalent above, or link it" >&2
+                echo "statically." >&2
+                exit 1
+              fi
+            done
+          '';
+        };
+
         nativelinkFor = p:
           (craneLibFor p).buildPackage ((commonArgsFor p)
             // {
@@ -178,7 +232,8 @@
               # If you're testing Nativelink locally, doing a dev profile will
               # massively speedup build times. Just don't commit/push anything build with dev!
               # CARGO_PROFILE = "dev";
-            });
+            }
+            // pkgs.lib.optionalAttrs p.stdenv.targetPlatform.isDarwin (darwinSystemDylibArgs p));
 
         nativeTargetPkgs =
           if pkgs.stdenv.hostPlatform.system == "x86_64-linux"