diff --git a/apps/web/src/components/Sidebar.logic.test.ts b/apps/web/src/components/Sidebar.logic.test.ts
index 634d91e9d..16275c034 100644
--- a/apps/web/src/components/Sidebar.logic.test.ts
+++ b/apps/web/src/components/Sidebar.logic.test.ts
@@ -2,6 +2,7 @@ import { describe, expect, it } from "vitest";
 
 import {
   hasUnseenCompletion,
+  isContextMenuPointerDown,
   resolveThreadStatusPill,
   shouldClearThreadSelectionOnMouseDown,
 } from "./Sidebar.logic";
@@ -62,6 +63,35 @@ describe("shouldClearThreadSelectionOnMouseDown", () => {
   });
 });
 
+describe("isContextMenuPointerDown", () => {
+  it("treats secondary-button pointerdown as a context-menu gesture", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 2,
+        ctrlKey: false,
+      }),
+    ).toBe(true);
+  });
+
+  it("treats ctrl-primary-click as a context-menu gesture", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 0,
+        ctrlKey: true,
+      }),
+    ).toBe(true);
+  });
+
+  it("does not treat primary-button pointerdown as a context-menu gesture", () => {
+    expect(
+      isContextMenuPointerDown({
+        button: 0,
+        ctrlKey: 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 f1afa0f64..e1cb4ea04 100644
--- a/apps/web/src/components/Sidebar.logic.ts
+++ b/apps/web/src/components/Sidebar.logic.ts
@@ -37,6 +37,11 @@ export function shouldClearThreadSelectionOnMouseDown(target: HTMLElement | null
   return !target.closest(THREAD_SELECTION_SAFE_SELECTOR);
 }
 
+export function isContextMenuPointerDown(input: { button: number; ctrlKey: boolean }): boolean {
+  if (input.button === 2) return true;
+  return input.button === 0 && input.ctrlKey;
+}
+
 export function resolveThreadStatusPill(input: {
   thread: ThreadStatusInput;
   hasPendingApprovals: boolean;
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 8b68c3b80..a8bdbf43c 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -10,7 +10,15 @@ import {
   TerminalIcon,
   TriangleAlertIcon,
 } from "lucide-react";
-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,
@@ -83,7 +91,11 @@ import {
 import { useThreadSelectionStore } from "../threadSelectionStore";
 import { formatWorktreePathForDisplay, getOrphanedWorktreePathForThread } from "../worktreeCleanup";
 import { isNonEmpty as isNonEmptyString } from "effect/String";
-import { resolveThreadStatusPill, shouldClearThreadSelectionOnMouseDown } from "./Sidebar.logic";
+import {
+  isContextMenuPointerDown,
+  resolveThreadStatusPill,
+  shouldClearThreadSelectionOnMouseDown,
+} from "./Sidebar.logic";
 
 const EMPTY_KEYBINDINGS: ResolvedKeybindingsConfig = [];
 const THREAD_PREVIEW_LIMIT = 6;
@@ -301,6 +313,7 @@ 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);
@@ -998,12 +1011,32 @@ export default function Sidebar() {
     dragInProgressRef.current = false;
   }, []);
 
-  const handleProjectTitlePointerDownCapture = useCallback(() => {
-    suppressProjectClickAfterDragRef.current = false;
-  }, []);
+  const handleProjectTitlePointerDownCapture = useCallback(
+    (event: PointerEvent<HTMLButtonElement>) => {
+      suppressProjectClickForContextMenuRef.current = false;
+      if (
+        isContextMenuPointerDown({
+          button: event.button,
+          ctrlKey: event.ctrlKey,
+        })
+      ) {
+        // Keep context-menu gestures from arming the sortable drag sensor.
+        event.stopPropagation();
+      }
+
+      suppressProjectClickAfterDragRef.current = false;
+    },
+    [],
+  );
 
   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();
@@ -1453,6 +1486,7 @@ 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,