diff --git a/apps/web/src/components/Sidebar.logic.ts b/apps/web/src/components/Sidebar.logic.ts
index c65ef8379..074bf2c30 100644
--- a/apps/web/src/components/Sidebar.logic.ts
+++ b/apps/web/src/components/Sidebar.logic.ts
@@ -39,6 +39,15 @@ export function shouldClearThreadSelectionOnMouseDown(target: HTMLElement | null
   return !target.closest(THREAD_SELECTION_SAFE_SELECTOR);
 }
 
+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 resolveSidebarNewThreadEnvMode(input: {
   requestedEnvMode?: SidebarNewThreadEnvMode;
   defaultEnvMode: SidebarNewThreadEnvMode;
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 1b43eb4c1..717f9d959 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,
@@ -84,6 +92,7 @@ import { useThreadSelectionStore } from "../threadSelectionStore";
 import { formatWorktreePathForDisplay, getOrphanedWorktreePathForThread } from "../worktreeCleanup";
 import { isNonEmpty as isNonEmptyString } from "effect/String";
 import {
+  isContextMenuPointerDown,
   resolveSidebarNewThreadEnvMode,
   resolveThreadRowClassName,
   resolveThreadStatusPill,
@@ -298,6 +307,7 @@ 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);
@@ -911,12 +921,33 @@ 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,
+          isMac: isMacPlatform(navigator.platform),
+        })
+      ) {
+        // 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();
@@ -1324,6 +1355,7 @@ 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,