diff --git a/extensions/matrix/src/matrix/monitor/handler.test-helpers.ts b/extensions/matrix/src/matrix/monitor/handler.test-helpers.ts
index b0d486e090f..b75ad343ed3 100644
--- a/extensions/matrix/src/matrix/monitor/handler.test-helpers.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.test-helpers.ts
@@ -23,6 +23,7 @@ type MatrixHandlerTestHarnessOptions = {
   accountId?: string;
   accountConfig?: MatrixConfig;
   cfg?: unknown;
+  liveCfg?: unknown;
   client?: Partial<MatrixClient>;
   runtime?: RuntimeEnv;
   logger?: RuntimeLogger;
@@ -192,7 +193,7 @@ export function createMatrixHandlerTestHarness(
     } as never,
     core: {
       config: {
-        current: () => cfgForHandler,
+        current: () => options.liveCfg ?? cfgForHandler,
       },
       channel: {
         pairing: {
diff --git a/extensions/matrix/src/matrix/monitor/handler.test.ts b/extensions/matrix/src/matrix/monitor/handler.test.ts
index a8278f4ce8c..d9036d85935 100644
--- a/extensions/matrix/src/matrix/monitor/handler.test.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.test.ts
@@ -228,6 +228,50 @@ describe("matrix monitor handler pairing account scope", () => {
     );
   });
 
+  it("uses live dmScope when deciding whether to pin main DM route updates", async () => {
+    const startupCfg = {
+      session: { dmScope: "main" },
+      channels: {
+        matrix: {
+          dm: { allowFrom: ["@owner:example.org"] },
+        },
+      },
+    };
+    const liveCfg = {
+      session: { dmScope: "per-channel-peer" },
+      channels: {
+        matrix: {
+          dm: { allowFrom: ["@owner:example.org"] },
+        },
+      },
+    };
+    const { handler, recordInboundSession } = createMatrixHandlerTestHarness({
+      cfg: startupCfg,
+      liveCfg,
+      dmPolicy: "allowlist",
+      allowFrom: ["@owner:example.org"],
+      allowFromResolvedEntries: [{ input: "@owner:example.org", id: "@owner:example.org" }],
+      isDirectMessage: true,
+    });
+
+    await handler(
+      "!dm:example.org",
+      createMatrixTextMessageEvent({
+        eventId: "$owner-dm-live-scope",
+        sender: "@owner:example.org",
+        body: "hello",
+      }),
+    );
+
+    expect(recordInboundSession).toHaveBeenCalledWith(
+      expect.objectContaining({
+        updateLastRoute: expect.objectContaining({
+          mainDmOwnerPin: undefined,
+        }),
+      }),
+    );
+  });
+
   it("sends pairing reminders for pending requests with cooldown", async () => {
     vi.useFakeTimers();
     vi.setSystemTime(new Date("2026-03-01T10:00:00.000Z"));
diff --git a/extensions/matrix/src/matrix/monitor/handler.ts b/extensions/matrix/src/matrix/monitor/handler.ts
index da1ee646f23..7527397b1f1 100644
--- a/extensions/matrix/src/matrix/monitor/handler.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.ts
@@ -1956,7 +1956,7 @@ export function createMatrixRoomMessageHandler(params: MatrixMonitorHandlerParam
               },
             });
             return resolvePinnedMainDmOwnerFromAllowlist({
-              dmScope: cfg.session?.dmScope,
+              dmScope: livePinnedCfg.session?.dmScope,
               allowFrom: livePinnedDmAllowFrom,
               normalizeEntry: normalizeMatrixUserId,
             });