diff --git a/desktop/src/features/agents/observerRelayStore.ts b/desktop/src/features/agents/observerRelayStore.ts
index 6aa397edb..213cefa19 100644
--- a/desktop/src/features/agents/observerRelayStore.ts
+++ b/desktop/src/features/agents/observerRelayStore.ts
@@ -128,6 +128,16 @@ function observerTag(event: RelayEvent, tagName: string) {
   return event.tags.find((tag) => tag[0] === tagName)?.[1] ?? null;
 }
 
+function pillDiagBridgeAgents(
+  agents: readonly Pick<ManagedAgent, "pubkey" | "status">[],
+) {
+  return agents.map((agent) => ({
+    pubkey: normalizePubkey(agent.pubkey),
+    status: agent.status,
+    startsObserver: agent.status === "running" || agent.status === "deployed",
+  }));
+}
+
 function appendAgentEvent(agentPubkey: string, event: ObserverEvent) {
   const key = normalizePubkey(agentPubkey);
   const current = eventsByAgent.get(key) ?? [];
@@ -390,6 +400,13 @@ export function useManagedAgentObserverBridge(
     [agents],
   );
 
+  console.log("[pill-diag] observer bridge render", {
+    subscriptionId,
+    hasActiveAgent,
+    agents: pillDiagBridgeAgents(agents),
+    at: new Date().toISOString(),
+  });
+
   const agentPubkeys = React.useMemo(
     () => agents.map((agent) => agent.pubkey),
     [agents],
diff --git a/desktop/src/features/sidebar/lib/useActiveWorkingChannelsById.ts b/desktop/src/features/sidebar/lib/useActiveWorkingChannelsById.ts
index dc0de7f4d..81aa5b323 100644
--- a/desktop/src/features/sidebar/lib/useActiveWorkingChannelsById.ts
+++ b/desktop/src/features/sidebar/lib/useActiveWorkingChannelsById.ts
@@ -22,6 +22,9 @@ import { normalizePubkey } from "@/shared/lib/pubkey";
 
 type WorkingAgentName = Pick<ManagedAgent, "pubkey" | "name">;
 type WorkingAgent = Pick<ManagedAgent, "pubkey" | "name" | "status">;
+type PillDiagProfile = UserProfileSummary & {
+  pubkey?: string;
+};
 type OwnedRelayWorkingAgent = Pick<RelayAgent, "pubkey" | "name"> & {
   status: "deployed";
 };
@@ -85,6 +88,86 @@ export function mergeWorkingAgents(
   return [...mergedByPubkey.values()];
 }
 
+function summarizeAgent(agent: WorkingAgentName & { status?: string }) {
+  return {
+    pubkey: normalizePubkey(agent.pubkey),
+    name: agent.name,
+    status: agent.status ?? null,
+  };
+}
+
+function summarizeRelayProfile(
+  pubkey: string,
+  profile: PillDiagProfile | undefined,
+  currentPubkey: string | undefined,
+) {
+  return {
+    pubkey: normalizePubkey(pubkey),
+    profileKeyPubkey: profile?.pubkey ? normalizePubkey(profile.pubkey) : null,
+    displayName: profile?.displayName ?? null,
+    isAgent: profile?.isAgent ?? null,
+    ownerPubkey: profile?.ownerPubkey
+      ? normalizePubkey(profile.ownerPubkey)
+      : null,
+    ownsAuthorAgent: ownsAuthorAgent(profile, currentPubkey),
+  };
+}
+
+function logPillDiagnostics({
+  currentPubkey,
+  managedAgents,
+  relayAgents,
+  profiles,
+  ownedRelayAgents,
+  workingAgents,
+  activeWorkingChannels,
+}: {
+  currentPubkey: string | undefined;
+  managedAgents: readonly WorkingAgent[];
+  relayAgents: readonly Pick<RelayAgent, "pubkey" | "name">[];
+  profiles: Record<string, UserProfileSummary> | undefined;
+  ownedRelayAgents: readonly WorkingAgent[];
+  workingAgents: readonly WorkingAgent[];
+  activeWorkingChannels: readonly ActiveChannelTurnSummary[];
+}) {
+  const normalizedProfiles = Object.fromEntries(
+    relayAgents.map((agent) => {
+      const pubkey = normalizePubkey(agent.pubkey);
+      const profile = profiles?.[pubkey] as PillDiagProfile | undefined;
+      return [
+        pubkey,
+        summarizeRelayProfile(agent.pubkey, profile, currentPubkey),
+      ];
+    }),
+  );
+
+  console.groupCollapsed("[pill-diag] active working channels inputs", {
+    currentPubkey: currentPubkey ? normalizePubkey(currentPubkey) : null,
+    managedAgentCount: managedAgents.length,
+    relayAgentCount: relayAgents.length,
+    ownedRelayAgentCount: ownedRelayAgents.length,
+    workingAgentCount: workingAgents.length,
+    activeChannelCount: activeWorkingChannels.length,
+  });
+  console.log("[pill-diag] currentPubkey", {
+    currentPubkey: currentPubkey ? normalizePubkey(currentPubkey) : null,
+  });
+  console.table(managedAgents.map(summarizeAgent));
+  console.log("[pill-diag] managedAgents", managedAgents.map(summarizeAgent));
+  console.table(relayAgents.map(summarizeAgent));
+  console.log("[pill-diag] relayAgents", relayAgents.map(summarizeAgent));
+  console.log("[pill-diag] profilesByRelayAgent", normalizedProfiles);
+  console.table(ownedRelayAgents.map(summarizeAgent));
+  console.log(
+    "[pill-diag] ownedRelayAgents",
+    ownedRelayAgents.map(summarizeAgent),
+  );
+  console.table(workingAgents.map(summarizeAgent));
+  console.log("[pill-diag] workingAgents", workingAgents.map(summarizeAgent));
+  console.log("[pill-diag] activeWorkingChannels", activeWorkingChannels);
+  console.groupEnd();
+}
+
 export function useActiveWorkingChannelsById(): ReadonlyMap<
   string,
   ActiveChannelTurnSummary
@@ -127,6 +210,26 @@ export function useActiveWorkingChannelsById(): ReadonlyMap<
 
   const activeWorkingChannels = useActiveAgentTurnsByChannel();
 
+  React.useEffect(() => {
+    logPillDiagnostics({
+      currentPubkey,
+      managedAgents,
+      relayAgents,
+      profiles: relayAgentProfilesQuery.data?.profiles,
+      ownedRelayAgents,
+      workingAgents,
+      activeWorkingChannels,
+    });
+  }, [
+    activeWorkingChannels,
+    currentPubkey,
+    managedAgents,
+    ownedRelayAgents,
+    relayAgentProfilesQuery.data?.profiles,
+    relayAgents,
+    workingAgents,
+  ]);
+
   return React.useMemo(
     () =>
       new Map(