diff --git a/package-lock.json b/package-lock.json
index d7cd4adf58..791c78c4d6 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1798,6 +1798,7 @@
       "os": [
         "aix"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1814,6 +1815,7 @@
       "os": [
         "android"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1830,6 +1832,7 @@
       "os": [
         "android"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1846,6 +1849,7 @@
       "os": [
         "android"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1862,6 +1866,7 @@
       "os": [
         "darwin"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1878,6 +1883,7 @@
       "os": [
         "darwin"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1894,6 +1900,7 @@
       "os": [
         "freebsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1910,6 +1917,7 @@
       "os": [
         "freebsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1926,6 +1934,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1942,6 +1951,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1958,6 +1968,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1974,6 +1985,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -1990,6 +2002,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2006,6 +2019,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2022,6 +2036,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2038,6 +2053,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2054,6 +2070,7 @@
       "os": [
         "linux"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2070,6 +2087,7 @@
       "os": [
         "netbsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2086,6 +2104,7 @@
       "os": [
         "netbsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2102,6 +2121,7 @@
       "os": [
         "openbsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2118,6 +2138,7 @@
       "os": [
         "openbsd"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2134,6 +2155,7 @@
       "os": [
         "openharmony"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2150,6 +2172,7 @@
       "os": [
         "sunos"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2166,6 +2189,7 @@
       "os": [
         "win32"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2182,6 +2206,7 @@
       "os": [
         "win32"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -2198,6 +2223,7 @@
       "os": [
         "win32"
       ],
+      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -4709,9 +4735,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -4728,9 +4751,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -4747,9 +4767,6 @@
       "cpu": [
         "ppc64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -4766,9 +4783,6 @@
       "cpu": [
         "s390x"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -4785,9 +4799,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -4804,9 +4815,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -5295,9 +5303,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -5314,9 +5319,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -5333,9 +5335,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -5352,9 +5351,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MIT",
       "optional": true,
       "os": [
@@ -5603,9 +5599,6 @@
         "arm64"
       ],
       "dev": true,
-      "libc": [
-        "glibc"
-      ],
       "license": "Apache-2.0 OR MIT",
       "optional": true,
       "os": [
@@ -5623,9 +5616,6 @@
         "arm64"
       ],
       "dev": true,
-      "libc": [
-        "musl"
-      ],
       "license": "Apache-2.0 OR MIT",
       "optional": true,
       "os": [
@@ -5643,9 +5633,6 @@
         "riscv64"
       ],
       "dev": true,
-      "libc": [
-        "glibc"
-      ],
       "license": "Apache-2.0 OR MIT",
       "optional": true,
       "os": [
@@ -5663,9 +5650,6 @@
         "x64"
       ],
       "dev": true,
-      "libc": [
-        "glibc"
-      ],
       "license": "Apache-2.0 OR MIT",
       "optional": true,
       "os": [
@@ -5683,9 +5667,6 @@
         "x64"
       ],
       "dev": true,
-      "libc": [
-        "musl"
-      ],
       "license": "Apache-2.0 OR MIT",
       "optional": true,
       "os": [
@@ -12196,9 +12177,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MPL-2.0",
       "optional": true,
       "os": [
@@ -12219,9 +12197,6 @@
       "cpu": [
         "arm64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MPL-2.0",
       "optional": true,
       "os": [
@@ -12242,9 +12217,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "glibc"
-      ],
       "license": "MPL-2.0",
       "optional": true,
       "os": [
@@ -12265,9 +12237,6 @@
       "cpu": [
         "x64"
       ],
-      "libc": [
-        "musl"
-      ],
       "license": "MPL-2.0",
       "optional": true,
       "os": [
@@ -16534,6 +16503,7 @@
       "os": [
         "darwin"
       ],
+      "peer": true,
       "engines": {
         "node": "^8.16.0 || ^10.6.0 || >=11.0.0"
       }
diff --git a/tests/tools/test_credential_files.py b/tests/tools/test_credential_files.py
index 09b11d6ea1..cb48d2a721 100644
--- a/tests/tools/test_credential_files.py
+++ b/tests/tools/test_credential_files.py
@@ -355,12 +355,22 @@ class TestCacheDirectoryMounts:
         assert "/root/.hermes/cache/images" in container_paths
 
     def test_empty_hermes_home(self, tmp_path, monkeypatch):
-        """No cache dirs → empty list."""
+        """Empty home → every staging dir is created and mounted (#76577).
+
+        Docker snapshots the mount list at container creation; skipping
+        not-yet-existing dirs meant the first attachment/clipboard file after
+        container start dangled forever. All _CACHE_DIRS entries mount."""
         hermes_home = tmp_path / ".hermes"
         hermes_home.mkdir()
         monkeypatch.setenv("HERMES_HOME", str(hermes_home))
 
-        assert get_cache_directory_mounts() == []
+        mounts = get_cache_directory_mounts()
+        container_paths = {m["container_path"] for m in mounts}
+        assert "/root/.hermes/attachments" in container_paths
+        assert "/root/.hermes/images" in container_paths
+        assert "/root/.hermes/cache/images" in container_paths
+        for mount in mounts:
+            assert Path(mount["host_path"]).is_dir()
 
     def test_images_upload_dir_is_mounted(self, tmp_path, monkeypatch):
         """The flat top-level ``images/`` upload dir is mounted (#69575).
@@ -412,12 +422,55 @@ class TestMapCachePathToContainer:
         )
 
 
-    def test_returns_none_when_no_cache_dirs_exist(self, tmp_path, monkeypatch):
+    def test_maps_path_even_when_cache_dir_missing(self, tmp_path, monkeypatch):
+        """Missing staging dirs are auto-created at mount-list time (#76577):
+        Docker snapshots mounts at container creation, so a dir that appears
+        later would dangle for the container's whole life. The map must
+        therefore succeed (and the dir exist) even before first use."""
         hermes_home = tmp_path / ".hermes"
         hermes_home.mkdir()
         monkeypatch.setenv("HERMES_HOME", str(hermes_home))
 
-        assert map_cache_path_to_container(str(hermes_home / "cache" / "images" / "x.png")) is None
+        mapped = map_cache_path_to_container(str(hermes_home / "cache" / "images" / "x.png"))
+        assert mapped == "/root/.hermes/cache/images/x.png"
+        assert (hermes_home / "cache" / "images").is_dir()
+
+
+class TestToAgentVisiblePathPerBackend:
+    """#76577 follow-up: translation covers every backend that relocates the
+    Hermes cache — not just docker — and skips the ones where the host path
+    stays correct (local; singularity auto-binds the host home)."""
+
+    def _staged(self, tmp_path, monkeypatch):
+        hermes_home = tmp_path / ".hermes"
+        (hermes_home / "attachments").mkdir(parents=True)
+        monkeypatch.setenv("HERMES_HOME", str(hermes_home))
+        return str(hermes_home / "attachments" / "drop.zip")
+
+    def test_docker_maps_to_root_hermes(self, tmp_path, monkeypatch):
+        staged = self._staged(tmp_path, monkeypatch)
+        monkeypatch.setenv("TERMINAL_ENV", "docker")
+        from tools.credential_files import to_agent_visible_cache_path
+        assert to_agent_visible_cache_path(staged) == "/root/.hermes/attachments/drop.zip"
+
+    def test_ssh_maps_to_tilde_hermes(self, tmp_path, monkeypatch):
+        staged = self._staged(tmp_path, monkeypatch)
+        monkeypatch.setenv("TERMINAL_ENV", "ssh")
+        from tools.credential_files import to_agent_visible_cache_path
+        assert to_agent_visible_cache_path(staged) == "~/.hermes/attachments/drop.zip"
+
+    @pytest.mark.parametrize("backend", ["local", "singularity", ""])
+    def test_untranslated_backends_keep_host_path(self, tmp_path, monkeypatch, backend):
+        staged = self._staged(tmp_path, monkeypatch)
+        monkeypatch.setenv("TERMINAL_ENV", backend)
+        from tools.credential_files import to_agent_visible_cache_path
+        assert to_agent_visible_cache_path(staged) == staged
+
+    def test_non_cache_path_passes_through(self, tmp_path, monkeypatch):
+        self._staged(tmp_path, monkeypatch)
+        monkeypatch.setenv("TERMINAL_ENV", "docker")
+        from tools.credential_files import to_agent_visible_cache_path
+        assert to_agent_visible_cache_path("/etc/hosts") == "/etc/hosts"
 
 
 class TestIterCacheFiles:
diff --git a/tools/credential_files.py b/tools/credential_files.py
index a0d5edb889..cd1234a92f 100644
--- a/tools/credential_files.py
+++ b/tools/credential_files.py
@@ -422,13 +422,25 @@ def get_cache_directory_mounts(
     mounts: List[Dict[str, str]] = []
     for new_subpath, old_name in _CACHE_DIRS:
         host_dir = get_hermes_dir(new_subpath, old_name)
-        if host_dir.is_dir():
-            # Always map to the *new* container layout regardless of host layout.
-            container_path = f"{container_base.rstrip('/')}/{new_subpath}"
-            mounts.append({
-                "host_path": str(host_dir),
-                "container_path": container_path,
-            })
+        if not host_dir.is_dir():
+            # Create missing staging dirs instead of skipping them: Docker
+            # snapshots this mount list at container CREATION, so a dir that
+            # appears later (first desktop attachment, first clipboard image)
+            # would dangle for the whole life of a persistent container
+            # (#76577). An empty bind-mounted dir costs nothing; a missing
+            # mount costs the feature. get_hermes_dir() already resolved
+            # new-vs-legacy layout, so creating its answer cannot shadow a
+            # populated legacy dir.
+            try:
+                host_dir.mkdir(parents=True, exist_ok=True)
+            except OSError:
+                continue  # unwritable home (tests, RO mounts) — skip as before
+        # Always map to the *new* container layout regardless of host layout.
+        container_path = f"{container_base.rstrip('/')}/{new_subpath}"
+        mounts.append({
+            "host_path": str(host_dir),
+            "container_path": container_path,
+        })
     return mounts
 
 
@@ -488,14 +500,33 @@ def to_agent_visible_cache_path(
 
     Returns the input unchanged if it is not under any auto-mounted cache
     directory, or if the active terminal backend does not require path
-    translation (only Docker for now).
+    translation (local).
+
+    Per-backend base (mirrors ``_agent_cache_base_for_env`` in
+    tools/image_generation_tool.py, the proven heuristics for where each
+    backend's Hermes cache lands):
+
+    * docker / modal — bind-mounted (docker) or per-file-synced (modal) at
+      ``/root/.hermes`` (the *container_base* default).
+    * ssh / daytona / vercel_sandbox — file-synced under the remote user's
+      home; ``~/.hermes`` is shell-expanded by the remote shell, so tool
+      commands resolve it regardless of the actual remote home. Previously
+      these backends synced the bytes but still rendered the dangling host
+      path (#76577 gap).
+    * singularity — NOT translated: Apptainer auto-binds the host home, so
+      the host path is directly readable and translation would dangle
+      (cache dirs are not remapped into that sandbox).
+
+    Backend is identified by TERMINAL_ENV (same env var
+    tools/terminal_tool.py reads in _get_environment_config).
     """
-    # Only Docker backend requires translation at this time.  Other backends
-    # (Modal, Daytona, Vercel) use different mount semantics and will be
-    # addressed separately if needed.  Backend is identified by TERMINAL_ENV
-    # (same env var tools/terminal_tool.py reads in _get_environment_config).
-    if os.environ.get("TERMINAL_ENV", "local") != "docker":
-        return host_path
+    backend = (os.environ.get("TERMINAL_ENV") or "local").strip().lower()
+    if backend in ("docker", "modal"):
+        pass  # /root/.hermes default
+    elif backend in ("ssh", "daytona", "vercel_sandbox"):
+        container_base = "~/.hermes"
+    else:
+        return host_path  # local, singularity, unknown: host path is correct
 
     mapped = map_cache_path_to_container(host_path, container_base=container_base)
     return mapped if mapped is not None else host_path