diff --git a/gateway/run.py b/gateway/run.py
index 617a38418e..51c9c529fe 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -7645,13 +7645,14 @@ class GatewayRunner:
         from hermes_cli.debug import (
             _capture_dump, collect_debug_report,
             upload_to_pastebin, _schedule_auto_delete,
-            _GATEWAY_PRIVACY_NOTICE,
+            _GATEWAY_PRIVACY_NOTICE, _best_effort_sweep_expired_pastes,
         )
 
         loop = asyncio.get_running_loop()
 
         # Run blocking I/O (dump capture, log reads, uploads) in a thread.
         def _collect_and_upload():
+            _best_effort_sweep_expired_pastes()
             dump_text = _capture_dump()
             report = collect_debug_report(log_lines=200, dump_text=dump_text)
 
diff --git a/hermes_cli/debug.py b/hermes_cli/debug.py
index 348de59a9d..2e622b6331 100644
--- a/hermes_cli/debug.py
+++ b/hermes_cli/debug.py
@@ -148,6 +148,14 @@ def _sweep_expired_pastes(now: Optional[float] = None) -> tuple[int, int]:
     return (deleted, len(remaining))
 
 
+def _best_effort_sweep_expired_pastes() -> None:
+    """Attempt pending-paste cleanup without letting /debug fail offline."""
+    try:
+        _sweep_expired_pastes()
+    except Exception:
+        pass
+
+
 # ---------------------------------------------------------------------------
 # Privacy / delete helpers
 # ---------------------------------------------------------------------------
@@ -518,6 +526,8 @@ def collect_debug_report(
 
 def run_debug_share(args):
     """Collect debug report + full logs, upload each, print URLs."""
+    _best_effort_sweep_expired_pastes()
+
     log_lines = getattr(args, "lines", 200)
     expiry = getattr(args, "expire", 7)
     local_only = getattr(args, "local", False)
diff --git a/tests/gateway/test_debug_command.py b/tests/gateway/test_debug_command.py
new file mode 100644
index 0000000000..48cda30140
--- /dev/null
+++ b/tests/gateway/test_debug_command.py
@@ -0,0 +1,60 @@
+"""Tests for the gateway /debug command."""
+
+from unittest.mock import patch
+
+import pytest
+
+from gateway.config import GatewayConfig, Platform
+from gateway.platforms.base import MessageEvent
+from gateway.session import SessionSource
+
+
+def _make_event(text="/debug", platform=Platform.TELEGRAM,
+                user_id="12345", chat_id="67890"):
+    source = SessionSource(
+        platform=platform,
+        user_id=user_id,
+        chat_id=chat_id,
+        user_name="testuser",
+    )
+    return MessageEvent(text=text, source=source)
+
+
+def _make_runner():
+    from gateway.run import GatewayRunner
+
+    runner = object.__new__(GatewayRunner)
+    runner.config = GatewayConfig()
+    runner.adapters = {}
+    return runner
+
+
+class TestHandleDebugCommand:
+    @pytest.mark.asyncio
+    async def test_debug_sweeps_expired_pastes_before_upload(self):
+        runner = _make_runner()
+        event = _make_event()
+
+        with patch("hermes_cli.debug._sweep_expired_pastes", return_value=(0, 0)) as mock_sweep, \
+             patch("hermes_cli.debug._capture_dump", return_value="dump"), \
+             patch("hermes_cli.debug.collect_debug_report", return_value="report"), \
+             patch("hermes_cli.debug.upload_to_pastebin", return_value="https://paste.rs/report"), \
+             patch("hermes_cli.debug._schedule_auto_delete"):
+            result = await runner._handle_debug_command(event)
+
+        mock_sweep.assert_called_once()
+        assert "https://paste.rs/report" in result
+
+    @pytest.mark.asyncio
+    async def test_debug_survives_sweep_failure(self):
+        runner = _make_runner()
+        event = _make_event()
+
+        with patch("hermes_cli.debug._sweep_expired_pastes", side_effect=RuntimeError("offline")), \
+             patch("hermes_cli.debug._capture_dump", return_value="dump"), \
+             patch("hermes_cli.debug.collect_debug_report", return_value="report"), \
+             patch("hermes_cli.debug.upload_to_pastebin", return_value="https://paste.rs/report"), \
+             patch("hermes_cli.debug._schedule_auto_delete"):
+            result = await runner._handle_debug_command(event)
+
+        assert "https://paste.rs/report" in result
diff --git a/tests/hermes_cli/test_debug.py b/tests/hermes_cli/test_debug.py
index a72b2057cd..e89b9e5acd 100644
--- a/tests/hermes_cli/test_debug.py
+++ b/tests/hermes_cli/test_debug.py
@@ -283,6 +283,44 @@ class TestCollectDebugReport:
 class TestRunDebugShare:
     """Test the run_debug_share CLI handler."""
 
+    def test_share_sweeps_expired_pastes(self, hermes_home, capsys):
+        """Slash-command path should sweep old pending deletes before uploading."""
+        from hermes_cli.debug import run_debug_share
+
+        args = MagicMock()
+        args.lines = 50
+        args.expire = 7
+        args.local = False
+
+        with patch("hermes_cli.dump.run_dump"), \
+             patch("hermes_cli.debug._sweep_expired_pastes", return_value=(0, 0)) as mock_sweep, \
+             patch("hermes_cli.debug.upload_to_pastebin",
+                    return_value="https://paste.rs/test"):
+            run_debug_share(args)
+
+        mock_sweep.assert_called_once()
+        assert "Debug report uploaded" in capsys.readouterr().out
+
+    def test_share_survives_sweep_failure(self, hermes_home, capsys):
+        """Expired-paste cleanup is best-effort and must not block sharing."""
+        from hermes_cli.debug import run_debug_share
+
+        args = MagicMock()
+        args.lines = 50
+        args.expire = 7
+        args.local = False
+
+        with patch("hermes_cli.dump.run_dump"), \
+             patch(
+                 "hermes_cli.debug._sweep_expired_pastes",
+                 side_effect=RuntimeError("offline"),
+             ), \
+             patch("hermes_cli.debug.upload_to_pastebin",
+                    return_value="https://paste.rs/test"):
+            run_debug_share(args)
+
+        assert "https://paste.rs/test" in capsys.readouterr().out
+
     def test_local_flag_prints_full_logs(self, hermes_home, capsys):
         """--local prints the report plus full log contents."""
         from hermes_cli.debug import run_debug_share