diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1cbe70540ad..79a5dec0456 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -54,6 +54,7 @@ Docs: https://docs.openclaw.ai
 - Models/openai-codex GPT-5.4 forward-compat: use the GPT-5.4 1,050,000-token context window and 128,000 max tokens for `openai-codex/gpt-5.4` instead of inheriting stale legacy Codex limits in resolver fallbacks and model listing. (#37876) thanks @yuweuii.
 - Telegram/media downloads: time out only stalled body reads so polling recovers from hung file downloads without aborting slow downloads that are still streaming data. (#40098) thanks @tysoncung.
 - Telegram/DM routing: dedupe inbound Telegram DMs per agent instead of per session key so the same DM cannot trigger duplicate replies when both `agent:main:main` and `agent:main:telegram:direct:<id>` resolve for one agent. Fixes #40005. Supersedes #40116. (#40519) thanks @obviyus.
+- Matrix/DM routing: add safer fallback detection for broken `m.direct` homeservers, honor explicit room bindings over DM classification, and preserve room-bound agent selection for Matrix DM rooms. (#19736) Thanks @derbronko.
 
 ## 2026.3.7
 
diff --git a/extensions/matrix/src/matrix/monitor/direct.test.ts b/extensions/matrix/src/matrix/monitor/direct.test.ts
index 2f6471f4be3..298b3996837 100644
--- a/extensions/matrix/src/matrix/monitor/direct.test.ts
+++ b/extensions/matrix/src/matrix/monitor/direct.test.ts
@@ -1,65 +1,400 @@
-import type { MatrixClient } from "@vector-im/matrix-bot-sdk";
 import { describe, expect, it, vi } from "vitest";
 import { createDirectRoomTracker } from "./direct.js";
 
-function createMockClient(params: {
-  isDm?: boolean;
-  senderDirect?: boolean;
-  selfDirect?: boolean;
-  members?: string[];
+// ---------------------------------------------------------------------------
+// Helpers -- minimal MatrixClient stub
+// ---------------------------------------------------------------------------
+
+type StateEvent = Record<string, unknown>;
+type DmMap = Record<string, boolean>;
+
+function createMockClient(opts: {
+  dmRooms?: DmMap;
+  membersByRoom?: Record<string, string[]>;
+  stateEvents?: Record<string, StateEvent>;
+  selfUserId?: string;
 }) {
-  const members = params.members ?? ["@alice:example.org", "@bot:example.org"];
+  const {
+    dmRooms = {},
+    membersByRoom = {},
+    stateEvents = {},
+    selfUserId = "@bot:example.org",
+  } = opts;
+
   return {
     dms: {
+      isDm: (roomId: string) => dmRooms[roomId] ?? false,
       update: vi.fn().mockResolvedValue(undefined),
-      isDm: vi.fn().mockReturnValue(params.isDm === true),
     },
-    getUserId: vi.fn().mockResolvedValue("@bot:example.org"),
-    getJoinedRoomMembers: vi.fn().mockResolvedValue(members),
+    getUserId: vi.fn().mockResolvedValue(selfUserId),
+    getJoinedRoomMembers: vi.fn().mockImplementation(async (roomId: string) => {
+      return membersByRoom[roomId] ?? [];
+    }),
     getRoomStateEvent: vi
       .fn()
-      .mockImplementation(async (_roomId: string, _event: string, stateKey: string) => {
-        if (stateKey === "@alice:example.org") {
-          return { is_direct: params.senderDirect === true };
+      .mockImplementation(async (roomId: string, eventType: string, stateKey: string) => {
+        const key = `${roomId}|${eventType}|${stateKey}`;
+        const ev = stateEvents[key];
+        if (ev === undefined) {
+          // Simulate real homeserver M_NOT_FOUND response (matches MatrixError shape)
+          const err = new Error(`State event not found: ${key}`) as Error & {
+            errcode?: string;
+            statusCode?: number;
+          };
+          err.errcode = "M_NOT_FOUND";
+          err.statusCode = 404;
+          throw err;
         }
-        if (stateKey === "@bot:example.org") {
-          return { is_direct: params.selfDirect === true };
-        }
-        return {};
+        return ev;
       }),
-  } as unknown as MatrixClient;
+  };
 }
 
+// ---------------------------------------------------------------------------
+// Tests -- isDirectMessage
+// ---------------------------------------------------------------------------
+
 describe("createDirectRoomTracker", () => {
-  it("treats m.direct rooms as DMs", async () => {
-    const tracker = createDirectRoomTracker(createMockClient({ isDm: true }));
-    await expect(
-      tracker.isDirectMessage({
-        roomId: "!room:example.org",
+  describe("m.direct detection (SDK DM cache)", () => {
+    it("returns true when SDK DM cache marks room as DM", async () => {
+      const client = createMockClient({
+        dmRooms: { "!dm:example.org": true },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!dm:example.org",
         senderId: "@alice:example.org",
-      }),
-    ).resolves.toBe(true);
+      });
+
+      expect(result).toBe(true);
+    });
+
+    it("returns false for rooms not in SDK DM cache (with >2 members)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!group:example.org": ["@alice:example.org", "@bob:example.org", "@carol:example.org"],
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!group:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(false);
+    });
   });
 
-  it("does not classify 2-member rooms as DMs without direct flags", async () => {
-    const client = createMockClient({ isDm: false });
-    const tracker = createDirectRoomTracker(client);
-    await expect(
-      tracker.isDirectMessage({
+  describe("is_direct state flag detection", () => {
+    it("returns true when sender's membership has is_direct=true", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: { "!room:example.org": ["@alice:example.org", "@bot:example.org"] },
+        stateEvents: {
+          "!room:example.org|m.room.member|@alice:example.org": { is_direct: true },
+          "!room:example.org|m.room.member|@bot:example.org": { is_direct: false },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
         roomId: "!room:example.org",
         senderId: "@alice:example.org",
-      }),
-    ).resolves.toBe(false);
-    expect(client.getJoinedRoomMembers).not.toHaveBeenCalled();
+      });
+
+      expect(result).toBe(true);
+    });
+
+    it("returns true when bot's own membership has is_direct=true", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: { "!room:example.org": ["@alice:example.org", "@bot:example.org"] },
+        stateEvents: {
+          "!room:example.org|m.room.member|@alice:example.org": { is_direct: false },
+          "!room:example.org|m.room.member|@bot:example.org": { is_direct: true },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!room:example.org",
+        senderId: "@alice:example.org",
+        selfUserId: "@bot:example.org",
+      });
+
+      expect(result).toBe(true);
+    });
   });
 
-  it("uses is_direct member flags when present", async () => {
-    const tracker = createDirectRoomTracker(createMockClient({ senderDirect: true }));
-    await expect(
-      tracker.isDirectMessage({
+  describe("conservative fallback (memberCount + room name)", () => {
+    it("returns true for 2-member room WITHOUT a room name (broken flags)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!broken-dm:example.org": ["@alice:example.org", "@bot:example.org"],
+        },
+        stateEvents: {
+          // is_direct not set on either member (e.g. Continuwuity bug)
+          "!broken-dm:example.org|m.room.member|@alice:example.org": {},
+          "!broken-dm:example.org|m.room.member|@bot:example.org": {},
+          // No m.room.name -> getRoomStateEvent will throw (event not found)
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!broken-dm:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(true);
+    });
+
+    it("returns true for 2-member room with empty room name", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!broken-dm:example.org": ["@alice:example.org", "@bot:example.org"],
+        },
+        stateEvents: {
+          "!broken-dm:example.org|m.room.member|@alice:example.org": {},
+          "!broken-dm:example.org|m.room.member|@bot:example.org": {},
+          "!broken-dm:example.org|m.room.name|": { name: "" },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!broken-dm:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(true);
+    });
+
+    it("returns false for 2-member room WITH a room name (named group)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!named-group:example.org": ["@alice:example.org", "@bob:example.org"],
+        },
+        stateEvents: {
+          "!named-group:example.org|m.room.member|@alice:example.org": {},
+          "!named-group:example.org|m.room.member|@bob:example.org": {},
+          "!named-group:example.org|m.room.name|": { name: "Project Alpha" },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!named-group:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(false);
+    });
+
+    it("returns false for 3+ member room without any DM signals", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!group:example.org": ["@alice:example.org", "@bob:example.org", "@carol:example.org"],
+        },
+        stateEvents: {
+          "!group:example.org|m.room.member|@alice:example.org": {},
+          "!group:example.org|m.room.member|@bob:example.org": {},
+          "!group:example.org|m.room.member|@carol:example.org": {},
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!group:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(false);
+    });
+
+    it("returns false for 1-member room (self-chat)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!solo:example.org": ["@bot:example.org"],
+        },
+        stateEvents: {
+          "!solo:example.org|m.room.member|@bot:example.org": {},
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!solo:example.org",
+        senderId: "@bot:example.org",
+      });
+
+      expect(result).toBe(false);
+    });
+  });
+
+  describe("detection priority", () => {
+    it("m.direct takes priority -- skips state and fallback checks", async () => {
+      const client = createMockClient({
+        dmRooms: { "!dm:example.org": true },
+        membersByRoom: {
+          "!dm:example.org": ["@alice:example.org", "@bob:example.org", "@carol:example.org"],
+        },
+        stateEvents: {
+          "!dm:example.org|m.room.name|": { name: "Named Room" },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!dm:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(true);
+      // Should not have checked member state or room name
+      expect(client.getRoomStateEvent).not.toHaveBeenCalled();
+      expect(client.getJoinedRoomMembers).not.toHaveBeenCalled();
+    });
+
+    it("is_direct takes priority over fallback -- skips member count", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        stateEvents: {
+          "!room:example.org|m.room.member|@alice:example.org": { is_direct: true },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
         roomId: "!room:example.org",
         senderId: "@alice:example.org",
-      }),
-    ).resolves.toBe(true);
+      });
+
+      expect(result).toBe(true);
+      // Should not have checked member count
+      expect(client.getJoinedRoomMembers).not.toHaveBeenCalled();
+    });
+  });
+
+  describe("edge cases", () => {
+    it("handles member count API failure gracefully", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        stateEvents: {
+          "!failing:example.org|m.room.member|@alice:example.org": {},
+          "!failing:example.org|m.room.member|@bot:example.org": {},
+        },
+      });
+      client.getJoinedRoomMembers.mockRejectedValue(new Error("API unavailable"));
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!failing:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      // Cannot determine member count -> conservative: classify as group
+      expect(result).toBe(false);
+    });
+
+    it("treats M_NOT_FOUND for room name as no name (DM)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!no-name:example.org": ["@alice:example.org", "@bot:example.org"],
+        },
+        stateEvents: {
+          "!no-name:example.org|m.room.member|@alice:example.org": {},
+          "!no-name:example.org|m.room.member|@bot:example.org": {},
+          // m.room.name not in stateEvents -> mock throws generic Error
+        },
+      });
+      // Override to throw M_NOT_FOUND like a real homeserver
+      const originalImpl = client.getRoomStateEvent.getMockImplementation()!;
+      client.getRoomStateEvent.mockImplementation(
+        async (roomId: string, eventType: string, stateKey: string) => {
+          if (eventType === "m.room.name") {
+            const err = new Error("not found") as Error & {
+              errcode?: string;
+              statusCode?: number;
+            };
+            err.errcode = "M_NOT_FOUND";
+            err.statusCode = 404;
+            throw err;
+          }
+          return originalImpl(roomId, eventType, stateKey);
+        },
+      );
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!no-name:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(true);
+    });
+
+    it("treats non-404 room name errors as unknown (falls through to group)", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!error-room:example.org": ["@alice:example.org", "@bot:example.org"],
+        },
+        stateEvents: {
+          "!error-room:example.org|m.room.member|@alice:example.org": {},
+          "!error-room:example.org|m.room.member|@bot:example.org": {},
+        },
+      });
+      // Simulate a network/auth error (not M_NOT_FOUND)
+      const originalImpl = client.getRoomStateEvent.getMockImplementation()!;
+      client.getRoomStateEvent.mockImplementation(
+        async (roomId: string, eventType: string, stateKey: string) => {
+          if (eventType === "m.room.name") {
+            throw new Error("Connection refused");
+          }
+          return originalImpl(roomId, eventType, stateKey);
+        },
+      );
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!error-room:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      // Network error -> don't assume DM, classify as group
+      expect(result).toBe(false);
+    });
+
+    it("whitespace-only room name is treated as no name", async () => {
+      const client = createMockClient({
+        dmRooms: {},
+        membersByRoom: {
+          "!ws-name:example.org": ["@alice:example.org", "@bot:example.org"],
+        },
+        stateEvents: {
+          "!ws-name:example.org|m.room.member|@alice:example.org": {},
+          "!ws-name:example.org|m.room.member|@bot:example.org": {},
+          "!ws-name:example.org|m.room.name|": { name: "   " },
+        },
+      });
+      const tracker = createDirectRoomTracker(client as never);
+
+      const result = await tracker.isDirectMessage({
+        roomId: "!ws-name:example.org",
+        senderId: "@alice:example.org",
+      });
+
+      expect(result).toBe(true);
+    });
   });
 });
diff --git a/extensions/matrix/src/matrix/monitor/direct.ts b/extensions/matrix/src/matrix/monitor/direct.ts
index d938c57b4e5..43b935b35fa 100644
--- a/extensions/matrix/src/matrix/monitor/direct.ts
+++ b/extensions/matrix/src/matrix/monitor/direct.ts
@@ -13,14 +13,22 @@ type DirectRoomTrackerOptions = {
 
 const DM_CACHE_TTL_MS = 30_000;
 
+/**
+ * Check if an error is a Matrix M_NOT_FOUND response (missing state event).
+ * The bot-sdk throws MatrixError with errcode/statusCode on the error object.
+ */
+function isMatrixNotFoundError(err: unknown): boolean {
+  if (typeof err !== "object" || err === null) return false;
+  const e = err as { errcode?: string; statusCode?: number };
+  return e.errcode === "M_NOT_FOUND" || e.statusCode === 404;
+}
+
 export function createDirectRoomTracker(client: MatrixClient, opts: DirectRoomTrackerOptions = {}) {
   const log = opts.log ?? (() => {});
   const includeMemberCountInLogs = opts.includeMemberCountInLogs === true;
   let lastDmUpdateMs = 0;
   let cachedSelfUserId: string | null = null;
-  const memberCountCache = includeMemberCountInLogs
-    ? new Map<string, { count: number; ts: number }>()
-    : undefined;
+  const memberCountCache = new Map<string, { count: number; ts: number }>();
 
   const ensureSelfUserId = async (): Promise<string | null> => {
     if (cachedSelfUserId) {
@@ -48,9 +56,6 @@ export function createDirectRoomTracker(client: MatrixClient, opts: DirectRoomTr
   };
 
   const resolveMemberCount = async (roomId: string): Promise<number | null> => {
-    if (!memberCountCache) {
-      return null;
-    }
     const cached = memberCountCache.get(roomId);
     const now = Date.now();
     if (cached && now - cached.ts < DM_CACHE_TTL_MS) {
@@ -91,7 +96,6 @@ export function createDirectRoomTracker(client: MatrixClient, opts: DirectRoomTr
         return true;
       }
 
-      // Check m.room.member state for is_direct flag
       const selfUserId = params.selfUserId ?? (await ensureSelfUserId());
       const directViaState =
         (await hasDirectFlag(roomId, senderId)) || (await hasDirectFlag(roomId, selfUserId ?? ""));
@@ -100,16 +104,47 @@ export function createDirectRoomTracker(client: MatrixClient, opts: DirectRoomTr
         return true;
       }
 
-      // Member count alone is NOT a reliable DM indicator.
-      // Explicitly configured group rooms with 2 members (e.g. bot + one user)
-      // were being misclassified as DMs, causing messages to be routed through
-      // DM policy instead of group policy and silently dropped.
-      // See: https://github.com/openclaw/openclaw/issues/20145
+      // Conservative fallback: 2-member rooms without an explicit room name are likely
+      // DMs with broken m.direct / is_direct flags. This has been observed on Continuwuity
+      // where m.direct pointed to the wrong room and is_direct was never set on the invite.
+      // Unlike the removed heuristic, this requires two signals (member count + no name)
+      // to avoid false positives on named 2-person group rooms.
+      //
+      // Performance: member count is cached (resolveMemberCount). The room name state
+      // check is not cached but only runs for the subset of 2-member rooms that reach
+      // this fallback path (no m.direct, no is_direct). In typical deployments this is
+      // a small minority of rooms.
+      //
+      // Note: there is a narrow race where a room name is being set concurrently with
+      // this check. The consequence is a one-time misclassification that self-corrects
+      // on the next message (once the state event is synced). This is acceptable given
+      // the alternative of an additional API call on every message.
+      const memberCount = await resolveMemberCount(roomId);
+      if (memberCount === 2) {
+        try {
+          const nameState = await client.getRoomStateEvent(roomId, "m.room.name", "");
+          if (!nameState?.name?.trim()) {
+            log(`matrix: dm detected via fallback (2 members, no room name) room=${roomId}`);
+            return true;
+          }
+        } catch (err: unknown) {
+          // Missing state events (M_NOT_FOUND) are expected for unnamed rooms and
+          // strongly indicate a DM. Any other error (network, auth) is ambiguous,
+          // so we fall through to classify as group rather than guess.
+          if (isMatrixNotFoundError(err)) {
+            log(`matrix: dm detected via fallback (2 members, no room name) room=${roomId}`);
+            return true;
+          }
+          log(
+            `matrix: dm fallback skipped (room name check failed: ${String(err)}) room=${roomId}`,
+          );
+        }
+      }
+
       if (!includeMemberCountInLogs) {
         log(`matrix: dm check room=${roomId} result=group`);
         return false;
       }
-      const memberCount = await resolveMemberCount(roomId);
       log(`matrix: dm check room=${roomId} result=group members=${memberCount ?? "unknown"}`);
       return false;
     },
diff --git a/extensions/matrix/src/matrix/monitor/handler.body-for-agent.test.ts b/extensions/matrix/src/matrix/monitor/handler.body-for-agent.test.ts
index 83cab3b4780..15665563039 100644
--- a/extensions/matrix/src/matrix/monitor/handler.body-for-agent.test.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.body-for-agent.test.ts
@@ -1,7 +1,11 @@
 import type { MatrixClient } from "@vector-im/matrix-bot-sdk";
 import type { PluginRuntime, RuntimeEnv, RuntimeLogger } from "openclaw/plugin-sdk/matrix";
 import { describe, expect, it, vi } from "vitest";
-import { createMatrixRoomMessageHandler } from "./handler.js";
+import {
+  createMatrixRoomMessageHandler,
+  resolveMatrixBaseRouteSession,
+  shouldOverrideMatrixDmToGroup,
+} from "./handler.js";
 import { EventType, type MatrixRawEvent } from "./types.js";
 
 describe("createMatrixRoomMessageHandler BodyForAgent sender label", () => {
@@ -18,8 +22,15 @@ describe("createMatrixRoomMessageHandler BodyForAgent sender label", () => {
       channel: {
         pairing: {
           readAllowFromStore: vi.fn().mockResolvedValue([]),
+          upsertPairingRequest: vi.fn().mockResolvedValue(undefined),
         },
         routing: {
+          buildAgentSessionKey: vi
+            .fn()
+            .mockImplementation(
+              (params: { agentId: string; channel: string; peer?: { kind: string; id: string } }) =>
+                `agent:${params.agentId}:${params.channel}:${params.peer?.kind ?? "direct"}:${params.peer?.id ?? "unknown"}`,
+            ),
           resolveAgentRoute: vi.fn().mockReturnValue({
             agentId: "main",
             accountId: undefined,
@@ -139,4 +150,47 @@ describe("createMatrixRoomMessageHandler BodyForAgent sender label", () => {
       }),
     );
   });
+
+  it("uses room-scoped session keys for DM rooms matched via parentPeer binding", () => {
+    const buildAgentSessionKey = vi
+      .fn()
+      .mockReturnValue("agent:main:matrix:channel:!dmroom:example.org");
+
+    const resolved = resolveMatrixBaseRouteSession({
+      buildAgentSessionKey,
+      baseRoute: {
+        agentId: "main",
+        sessionKey: "agent:main:main",
+        mainSessionKey: "agent:main:main",
+        matchedBy: "binding.peer.parent",
+      },
+      isDirectMessage: true,
+      roomId: "!dmroom:example.org",
+      accountId: undefined,
+    });
+
+    expect(buildAgentSessionKey).toHaveBeenCalledWith({
+      agentId: "main",
+      channel: "matrix",
+      accountId: undefined,
+      peer: { kind: "channel", id: "!dmroom:example.org" },
+    });
+    expect(resolved).toEqual({
+      sessionKey: "agent:main:matrix:channel:!dmroom:example.org",
+      lastRoutePolicy: "session",
+    });
+  });
+
+  it("does not override DMs to groups for explicit allow:false room config", () => {
+    expect(
+      shouldOverrideMatrixDmToGroup({
+        isDirectMessage: true,
+        roomConfigInfo: {
+          config: { allow: false },
+          allowed: false,
+          matchSource: "direct",
+        },
+      }),
+    ).toBe(false);
+  });
 });
diff --git a/extensions/matrix/src/matrix/monitor/handler.ts b/extensions/matrix/src/matrix/monitor/handler.ts
index 295d61f2de0..0adc9fa2886 100644
--- a/extensions/matrix/src/matrix/monitor/handler.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.ts
@@ -77,6 +77,56 @@ export type MatrixMonitorHandlerParams = {
   accountId?: string | null;
 };
 
+export function resolveMatrixBaseRouteSession(params: {
+  buildAgentSessionKey: (params: {
+    agentId: string;
+    channel: string;
+    accountId?: string | null;
+    peer?: { kind: "direct" | "channel"; id: string } | null;
+  }) => string;
+  baseRoute: {
+    agentId: string;
+    sessionKey: string;
+    mainSessionKey: string;
+    matchedBy?: string;
+  };
+  isDirectMessage: boolean;
+  roomId: string;
+  accountId?: string | null;
+}): { sessionKey: string; lastRoutePolicy: "main" | "session" } {
+  const sessionKey =
+    params.isDirectMessage && params.baseRoute.matchedBy === "binding.peer.parent"
+      ? params.buildAgentSessionKey({
+          agentId: params.baseRoute.agentId,
+          channel: "matrix",
+          accountId: params.accountId,
+          peer: { kind: "channel", id: params.roomId },
+        })
+      : params.baseRoute.sessionKey;
+  return {
+    sessionKey,
+    lastRoutePolicy: sessionKey === params.baseRoute.mainSessionKey ? "main" : "session",
+  };
+}
+
+export function shouldOverrideMatrixDmToGroup(params: {
+  isDirectMessage: boolean;
+  roomConfigInfo?:
+    | {
+        config?: MatrixRoomConfig;
+        allowed: boolean;
+        matchSource?: string;
+      }
+    | undefined;
+}): boolean {
+  return (
+    params.isDirectMessage === true &&
+    params.roomConfigInfo?.config !== undefined &&
+    params.roomConfigInfo.allowed === true &&
+    params.roomConfigInfo.matchSource === "direct"
+  );
+}
+
 export function createMatrixRoomMessageHandler(params: MatrixMonitorHandlerParams) {
   const {
     client,
@@ -188,22 +238,37 @@ export function createMatrixRoomMessageHandler(params: MatrixMonitorHandlerParam
         }
       }
 
-      const isDirectMessage = await directTracker.isDirectMessage({
+      let isDirectMessage = await directTracker.isDirectMessage({
         roomId,
         senderId,
         selfUserId,
       });
+
+      // Resolve room config early so explicitly configured rooms can override DM classification.
+      // This ensures rooms in the groups config are always treated as groups regardless of
+      // member count or protocol-level DM flags. Only explicit matches (not wildcards) trigger
+      // the override to avoid breaking DM routing when a wildcard entry exists. (See #9106)
+      const roomConfigInfo = resolveMatrixRoomConfig({
+        rooms: roomsConfig,
+        roomId,
+        aliases: roomAliases,
+        name: roomName,
+      });
+      if (shouldOverrideMatrixDmToGroup({ isDirectMessage, roomConfigInfo })) {
+        logVerboseMessage(
+          `matrix: overriding DM to group for configured room=${roomId} (${roomConfigInfo.matchKey})`,
+        );
+        isDirectMessage = false;
+      }
+
       const isRoom = !isDirectMessage;
 
-      const roomConfigInfo = isRoom
-        ? resolveMatrixRoomConfig({
-            rooms: roomsConfig,
-            roomId,
-            aliases: roomAliases,
-            name: roomName,
-          })
-        : undefined;
-      const roomConfig = roomConfigInfo?.config;
+      if (isRoom && groupPolicy === "disabled") {
+        return;
+      }
+      // Only expose room config for confirmed group rooms. DMs should never inherit
+      // group settings (skills, systemPrompt, autoReply) even when a wildcard entry exists.
+      const roomConfig = isRoom ? roomConfigInfo?.config : undefined;
       const roomMatchMeta = roomConfigInfo
         ? `matchKey=${roomConfigInfo.matchKey ?? "none"} matchSource=${
             roomConfigInfo.matchSource ?? "none"
@@ -435,13 +500,24 @@ export function createMatrixRoomMessageHandler(params: MatrixMonitorHandlerParam
           kind: isDirectMessage ? "direct" : "channel",
           id: isDirectMessage ? senderId : roomId,
         },
+        // For DMs, pass roomId as parentPeer so the conversation is bindable by room ID
+        // while preserving DM trust semantics (secure 1:1, no group restrictions).
+        parentPeer: isDirectMessage ? { kind: "channel", id: roomId } : undefined,
+      });
+      const baseRouteSession = resolveMatrixBaseRouteSession({
+        buildAgentSessionKey: core.channel.routing.buildAgentSessionKey,
+        baseRoute,
+        isDirectMessage,
+        roomId,
+        accountId,
       });
 
       const route = {
         ...baseRoute,
+        lastRoutePolicy: baseRouteSession.lastRoutePolicy,
         sessionKey: threadRootId
-          ? `${baseRoute.sessionKey}:thread:${threadRootId}`
-          : baseRoute.sessionKey,
+          ? `${baseRouteSession.sessionKey}:thread:${threadRootId}`
+          : baseRouteSession.sessionKey,
       };
 
       let threadStarterBody: string | undefined;
diff --git a/extensions/matrix/src/matrix/monitor/rooms.test.ts b/extensions/matrix/src/matrix/monitor/rooms.test.ts
index 21fe5a90474..9c94dc49ce0 100644
--- a/extensions/matrix/src/matrix/monitor/rooms.test.ts
+++ b/extensions/matrix/src/matrix/monitor/rooms.test.ts
@@ -36,4 +36,89 @@ describe("resolveMatrixRoomConfig", () => {
     expect(byName.allowed).toBe(false);
     expect(byName.config).toBeUndefined();
   });
+
+  describe("matchSource classification", () => {
+    it('returns matchSource="direct" for exact room ID match', () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: { "!room:example.org": { allow: true } },
+        roomId: "!room:example.org",
+        aliases: [],
+      });
+      expect(result.matchSource).toBe("direct");
+      expect(result.config).toBeDefined();
+    });
+
+    it('returns matchSource="direct" for alias match', () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: { "#alias:example.org": { allow: true } },
+        roomId: "!room:example.org",
+        aliases: ["#alias:example.org"],
+      });
+      expect(result.matchSource).toBe("direct");
+      expect(result.config).toBeDefined();
+    });
+
+    it('returns matchSource="wildcard" for wildcard match', () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: { "*": { allow: true } },
+        roomId: "!any:example.org",
+        aliases: [],
+      });
+      expect(result.matchSource).toBe("wildcard");
+      expect(result.config).toBeDefined();
+    });
+
+    it("returns undefined matchSource when no match", () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: { "!other:example.org": { allow: true } },
+        roomId: "!room:example.org",
+        aliases: [],
+      });
+      expect(result.matchSource).toBeUndefined();
+      expect(result.config).toBeUndefined();
+    });
+
+    it("direct match takes priority over wildcard", () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: {
+          "!room:example.org": { allow: true, systemPrompt: "room-specific" },
+          "*": { allow: true, systemPrompt: "generic" },
+        },
+        roomId: "!room:example.org",
+        aliases: [],
+      });
+      expect(result.matchSource).toBe("direct");
+      expect(result.config?.systemPrompt).toBe("room-specific");
+    });
+  });
+
+  describe("DM override safety (matchSource distinction)", () => {
+    // These tests verify the matchSource property that handler.ts uses
+    // to decide whether a configured room should override DM classification.
+    // Only "direct" matches should trigger the override -- never "wildcard".
+
+    it("wildcard config should NOT be usable to override DM classification", () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: { "*": { allow: true, skills: ["general"] } },
+        roomId: "!dm-room:example.org",
+        aliases: [],
+      });
+      // handler.ts checks: matchSource === "direct" -> this is "wildcard", so no override
+      expect(result.matchSource).not.toBe("direct");
+      expect(result.matchSource).toBe("wildcard");
+    });
+
+    it("explicitly configured room should be usable to override DM classification", () => {
+      const result = resolveMatrixRoomConfig({
+        rooms: {
+          "!configured-room:example.org": { allow: true },
+          "*": { allow: true },
+        },
+        roomId: "!configured-room:example.org",
+        aliases: [],
+      });
+      // handler.ts checks: matchSource === "direct" -> this IS "direct", so override is safe
+      expect(result.matchSource).toBe("direct");
+    });
+  });
 });