diff --git a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/ask/request.py b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/ask/request.py
index d61d38f34..a725bfee1 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/ask/request.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/ask/request.py
@@ -17,6 +17,7 @@ from langchain_core.tools import BaseTool
 from langgraph.types import interrupt
 
 from app.agents.new_chat.permissions import Rule
+from app.observability import metrics as ot_metrics
 from app.observability import otel as ot
 
 from .decision import normalize_permission_decision
@@ -52,6 +53,8 @@ def request_permission_decision(
         ),
         ot.interrupt_span(interrupt_type=PERMISSION_ASK_INTERRUPT_TYPE),
     ):
+        ot_metrics.record_permission_ask(permission=tool_name)
+        ot_metrics.record_interrupt(interrupt_type=PERMISSION_ASK_INTERRUPT_TYPE)
         decision = interrupt(payload)
     return normalize_permission_decision(decision)
 
diff --git a/surfsense_backend/app/agents/new_chat/middleware/compaction.py b/surfsense_backend/app/agents/new_chat/middleware/compaction.py
index 16361e16b..8173976fe 100644
--- a/surfsense_backend/app/agents/new_chat/middleware/compaction.py
+++ b/surfsense_backend/app/agents/new_chat/middleware/compaction.py
@@ -34,6 +34,7 @@ from deepagents.middleware.summarization import (
 )
 from langchain_core.messages import SystemMessage
 
+from app.observability import metrics as ot_metrics
 from app.observability import otel as ot
 
 if TYPE_CHECKING:
@@ -178,6 +179,7 @@ class SurfSenseCompactionMiddleware(SummarizationMiddleware):
             messages_in=len(conversation_messages),
             extra={"compaction.cutoff_index": int(cutoff_index)},
         ):
+            ot_metrics.record_compaction_run(reason="auto")
             messages_to_summarize, preserved_messages = super()._partition_messages(
                 conversation_messages, cutoff_index
             )
diff --git a/surfsense_backend/app/agents/new_chat/middleware/doom_loop.py b/surfsense_backend/app/agents/new_chat/middleware/doom_loop.py
index 850ecd1d2..d50cadc0e 100644
--- a/surfsense_backend/app/agents/new_chat/middleware/doom_loop.py
+++ b/surfsense_backend/app/agents/new_chat/middleware/doom_loop.py
@@ -47,6 +47,7 @@ from langgraph.config import get_config
 from langgraph.runtime import Runtime
 from langgraph.types import interrupt
 
+from app.observability import metrics as ot_metrics
 from app.observability import otel as ot
 
 logger = logging.getLogger(__name__)
@@ -195,6 +196,7 @@ class DoomLoopMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, Respon
                 "interrupt.tool": (action or {}).get("tool", "<unknown>"),
             },
         ):
+            ot_metrics.record_interrupt(interrupt_type="permission_ask")
             decision = interrupt(
                 {
                     "type": "permission_ask",
diff --git a/surfsense_backend/app/agents/new_chat/middleware/permission.py b/surfsense_backend/app/agents/new_chat/middleware/permission.py
index f77b7e387..e174ab0bd 100644
--- a/surfsense_backend/app/agents/new_chat/middleware/permission.py
+++ b/surfsense_backend/app/agents/new_chat/middleware/permission.py
@@ -61,6 +61,7 @@ from app.agents.new_chat.permissions import (
     aggregate_action,
     evaluate_many,
 )
+from app.observability import metrics as ot_metrics
 from app.observability import otel as ot
 
 logger = logging.getLogger(__name__)
@@ -284,6 +285,8 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
             ),
             ot.interrupt_span(interrupt_type="permission_ask"),
         ):
+            ot_metrics.record_permission_ask(permission=tool_name)
+            ot_metrics.record_interrupt(interrupt_type="permission_ask")
             decision = interrupt(payload)
         return _normalize_permission_decision(decision)