diff --git a/nanobot/channels/slack.py b/nanobot/channels/slack.py
index 66ef6f3b..0bdeedc7 100644
--- a/nanobot/channels/slack.py
+++ b/nanobot/channels/slack.py
@@ -435,9 +435,9 @@ class SlackChannel(BaseChannel):
         marker = f"[{marker_type}: {name}]"
         url = str(file_info.get("url_private_download") or file_info.get("url_private") or "")
         if not url:
-            return None, f"[{marker_type}: {name}: missing download url]"
+            return None, self._download_failure_marker(marker_type, name, "missing download url")
         if not self.config.bot_token:
-            return None, f"[{marker_type}: {name}: missing bot token]"
+            return None, self._download_failure_marker(marker_type, name, "missing bot token")
 
         filename = safe_filename(f"{file_id}_{name}")
         path = Path(get_media_dir("slack")) / filename
@@ -454,7 +454,14 @@ class SlackChannel(BaseChannel):
             return str(path), marker
         except Exception as e:
             logger.warning("Failed to download Slack file {}: {}", file_id, e)
-            return None, f"[{marker_type}: {name}: download failed]"
+            return None, self._download_failure_marker(marker_type, name, "download failed")
+
+    @staticmethod
+    def _download_failure_marker(marker_type: str, name: str, reason: str) -> str:
+        return (
+            f"[{marker_type}: {name}: {reason}; not available to nanobot. "
+            "Check Slack files:read scope, reinstall the Slack app, and ensure the bot can access the file.]"
+        )
 
     @staticmethod
     def _looks_like_html_download(response: httpx.Response) -> bool:
diff --git a/tests/channels/test_slack_channel.py b/tests/channels/test_slack_channel.py
index 49ae3908..630685ee 100644
--- a/tests/channels/test_slack_channel.py
+++ b/tests/channels/test_slack_channel.py
@@ -643,6 +643,14 @@ def test_slack_download_rejects_login_html() -> None:
     assert SlackChannel._looks_like_html_download(markdown_response) is False
 
 
+def test_slack_download_failure_marker_is_actionable() -> None:
+    marker = SlackChannel._download_failure_marker("image", "screenshot.png", "download failed")
+
+    assert "not available to nanobot" in marker
+    assert "files:read" in marker
+    assert "reinstall the Slack app" in marker
+
+
 def test_slack_channel_uses_channel_aware_allow_policy() -> None:
     channel = SlackChannel(SlackConfig(enabled=True, allow_from=[]), MessageBus())
     assert channel.is_allowed("U1") is True
diff --git a/tests/utils/test_token_estimation.py b/tests/utils/test_token_estimation.py
new file mode 100644
index 00000000..c3257b31
--- /dev/null
+++ b/tests/utils/test_token_estimation.py
@@ -0,0 +1,32 @@
+from nanobot.utils.helpers import estimate_prompt_tokens_chain
+
+
+class _NoCounterProvider:
+    pass
+
+
+class _BrokenCounterProvider:
+    def estimate_prompt_tokens(self, messages, tools=None, model=None):
+        raise RuntimeError("counter unavailable")
+
+
+def test_estimate_prompt_tokens_chain_falls_back_without_provider_counter() -> None:
+    tokens, source = estimate_prompt_tokens_chain(
+        _NoCounterProvider(),
+        "test-model",
+        [{"role": "user", "content": "hello"}],
+    )
+
+    assert tokens > 0
+    assert source == "tiktoken"
+
+
+def test_estimate_prompt_tokens_chain_falls_back_when_provider_counter_fails() -> None:
+    tokens, source = estimate_prompt_tokens_chain(
+        _BrokenCounterProvider(),
+        "test-model",
+        [{"role": "user", "content": "hello"}],
+    )
+
+    assert tokens > 0
+    assert source == "tiktoken"