diff --git a/apps/web/src/components/Sidebar.logic.test.ts b/apps/web/src/components/Sidebar.logic.test.ts
index 0824758baa..cc49a82e69 100644
--- a/apps/web/src/components/Sidebar.logic.test.ts
+++ b/apps/web/src/components/Sidebar.logic.test.ts
@@ -5,6 +5,7 @@ import {
   getVisibleThreadsForProject,
   getProjectSortTimestamp,
   hasUnseenCompletion,
+  isContextMenuPointerDown,
   resolveProjectStatusIndicator,
   resolveSidebarNewThreadEnvMode,
   resolveThreadRowClassName,
@@ -96,6 +97,38 @@ describe("resolveSidebarNewThreadEnvMode", () => {
   });
 });
 
+describe("isContextMenuPointerDown", () => {
+  it("treats secondary-button presses as context menu gestures on all platforms", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 2,
+        ctrlKey: false,
+        isMac: false,
+      }),
+    ).toBe(true);
+  });
+
+  it("treats ctrl+primary-click as a context menu gesture on macOS", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 0,
+        ctrlKey: true,
+        isMac: true,
+      }),
+    ).toBe(true);
+  });
+
+  it("does not treat ctrl+primary-click as a context menu gesture off macOS", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 0,
+        ctrlKey: true,
+        isMac: false,
+      }),
+    ).toBe(false);
+  });
+});
+
 describe("resolveThreadStatusPill", () => {
   const baseThread = {
     interactionMode: "plan" as const,
diff --git a/apps/web/src/components/Sidebar.logic.ts b/apps/web/src/components/Sidebar.logic.ts
index 6ca29d27e9..22a6268ac7 100644
--- a/apps/web/src/components/Sidebar.logic.ts
+++ b/apps/web/src/components/Sidebar.logic.ts
@@ -67,6 +67,15 @@ export function resolveSidebarNewThreadEnvMode(input: {
   return input.requestedEnvMode ?? input.defaultEnvMode;
 }
 
+export function isContextMenuPointerDown(input: {
+  button: number;
+  ctrlKey: boolean;
+  isMac: boolean;
+}): boolean {
+  if (input.button === 2) return true;
+  return input.isMac && input.button === 0 && input.ctrlKey;
+}
+
 export function resolveThreadRowClassName(input: {
   isActive: boolean;
   isSelected: boolean;
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 299948c862..d6ef9fc819 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -13,7 +13,15 @@ import {
 } from "lucide-react";
 import { ProjectFavicon } from "./ProjectFavicon";
 import { autoAnimate } from "@formkit/auto-animate";
-import { useCallback, useEffect, useMemo, useRef, useState, type MouseEvent } from "react";
+import {
+  useCallback,
+  useEffect,
+  useMemo,
+  useRef,
+  useState,
+  type MouseEvent,
+  type PointerEvent,
+} from "react";
 import {
   DndContext,
   type DragCancelEvent,
@@ -93,6 +101,7 @@ import { useThreadSelectionStore } from "../threadSelectionStore";
 import { isNonEmpty as isNonEmptyString } from "effect/String";
 import {
   getVisibleThreadsForProject,
+  isContextMenuPointerDown,
   resolveProjectStatusIndicator,
   resolveSidebarNewThreadEnvMode,
   resolveThreadRowClassName,
@@ -348,6 +357,7 @@ export default function Sidebar() {
   const renamingInputRef = useRef<HTMLInputElement | null>(null);
   const dragInProgressRef = useRef(false);
   const suppressProjectClickAfterDragRef = useRef(false);
+  const suppressProjectClickForContextMenuRef = useRef(false);
   const [desktopUpdateState, setDesktopUpdateState] = useState<DesktopUpdateState | null>(null);
   const selectedThreadIds = useThreadSelectionStore((s) => s.selectedThreadIds);
   const toggleThreadSelection = useThreadSelectionStore((s) => s.toggleThread);
@@ -941,9 +951,24 @@ export default function Sidebar() {
     animatedThreadListsRef.current.add(node);
   }, []);
 
-  const handleProjectTitlePointerDownCapture = useCallback(() => {
-    suppressProjectClickAfterDragRef.current = false;
-  }, []);
+  const handleProjectTitlePointerDownCapture = useCallback(
+    (event: PointerEvent<HTMLButtonElement>) => {
+      suppressProjectClickForContextMenuRef.current = false;
+      if (
+        isContextMenuPointerDown({
+          button: event.button,
+          ctrlKey: event.ctrlKey,
+          isMac: isMacPlatform(navigator.platform),
+        })
+      ) {
+        // Keep context-menu gestures from arming the sortable drag sensor.
+        event.stopPropagation();
+      }
+
+      suppressProjectClickAfterDragRef.current = false;
+    },
+    [],
+  );
 
   const visibleThreads = useMemo(
     () => threads.filter((thread) => thread.archivedAt === null),
@@ -1242,6 +1267,7 @@ export default function Sidebar() {
             onKeyDown={(event) => handleProjectTitleKeyDown(event, project.id)}
             onContextMenu={(event) => {
               event.preventDefault();
+              suppressProjectClickForContextMenuRef.current = true;
               void handleProjectContextMenu(project.id, {
                 x: event.clientX,
                 y: event.clientY,
@@ -1351,6 +1377,12 @@ export default function Sidebar() {
 
   const handleProjectTitleClick = useCallback(
     (event: React.MouseEvent<HTMLButtonElement>, projectId: ProjectId) => {
+      if (suppressProjectClickForContextMenuRef.current) {
+        suppressProjectClickForContextMenuRef.current = false;
+        event.preventDefault();
+        event.stopPropagation();
+        return;
+      }
       if (dragInProgressRef.current) {
         event.preventDefault();
         event.stopPropagation();