diff --git a/packages/app/src/context/layout.tsx b/packages/app/src/context/layout.tsx
index 5199e5a26be..48fd53c2074 100644
--- a/packages/app/src/context/layout.tsx
+++ b/packages/app/src/context/layout.tsx
@@ -90,6 +90,25 @@ export function pruneSessionKeys(input: {
     .slice(input.max)
 }
 
+type RootResult = {
+  root: string
+  project?: {
+    id?: string
+    worktree?: string
+    vcs?: string
+    sandboxes?: string[]
+  }
+}
+
+const norm = (dir: string) => {
+  const drive = dir.match(/^([A-Za-z]:)[\\/]+$/)
+  if (drive) return `${drive[1].toLowerCase()}/`
+  if (/^[\\/]+$/.test(dir)) return "/"
+  const key = dir.replace(/[\\/]+$/, "").replaceAll("\\", "/")
+  if (/^[A-Za-z]:\//.test(key) || key.startsWith("//")) return key.toLowerCase()
+  return key
+}
+
 function nextSessionTabsForOpen(current: SessionTabs | undefined, tab: string): SessionTabs {
   const all = current?.all ?? []
   if (tab === "review") return { all: all.filter((x) => x !== "review"), active: tab }
@@ -457,9 +476,30 @@ export const { use: useLayout, provider: LayoutProvider } = createSimpleContext(
       return directory
     }
 
+    const resolveRoot = (directory: string): Promise<RootResult> => {
+      return globalSdk
+        .createClient({ directory, throwOnError: true })
+        .project.current()
+        .then((x) => {
+          const project = x.data
+          return {
+            root: project?.worktree && project.id !== "global" ? project.worktree : directory,
+            project: project
+              ? {
+                  id: project.id,
+                  worktree: project.worktree,
+                  vcs: project.vcs,
+                  sandboxes: project.sandboxes,
+                }
+              : undefined,
+          }
+        })
+        .catch(() => ({ root: directory }))
+    }
+
     createEffect(() => {
       const projects = server.projects.list()
-      const seen = new Set(projects.map((project) => project.worktree))
+      const seen = new Set(projects.map((project) => norm(project.worktree)))
 
       batch(() => {
         for (const project of projects) {
@@ -468,9 +508,10 @@ export const { use: useLayout, provider: LayoutProvider } = createSimpleContext(
 
           server.projects.close(project.worktree)
 
-          if (!seen.has(root)) {
+          const key = norm(root)
+          if (!seen.has(key)) {
             server.projects.open(root)
-            seen.add(root)
+            seen.add(key)
           }
 
           if (project.expanded) server.projects.expand(root)
@@ -565,11 +606,18 @@ export const { use: useLayout, provider: LayoutProvider } = createSimpleContext(
       },
       projects: {
         list,
-        open(directory: string) {
-          const root = rootFor(directory)
-          if (server.projects.list().find((x) => x.worktree === root)) return
+        resolve(directory: string) {
+          return resolveRoot(directory)
+        },
+        async open(directory: string, resolved?: RootResult) {
+          const value = resolved ?? (await resolveRoot(directory))
+          const root = value.root
+          const key = norm(root)
+          const exists = server.projects.list().some((x) => norm(x.worktree) === key)
+          if (exists) return value
           globalSync.project.loadSessions(root)
           server.projects.open(root)
+          return value
         },
         close(directory: string) {
           server.projects.close(directory)
diff --git a/packages/app/src/pages/layout.tsx b/packages/app/src/pages/layout.tsx
index 052a03c5491..50e857f1c0b 100644
--- a/packages/app/src/pages/layout.tsx
+++ b/packages/app/src/pages/layout.tsx
@@ -1262,20 +1262,28 @@ export default function Layout(props: ParentProps) {
     navigateWithSidebarReset(`/${base64Encode(session.directory)}/session/${session.id}`)
   }
 
-  function openProject(directory: string, navigate = true) {
-    layout.projects.open(directory)
-    if (navigate) navigateToProject(directory)
+  async function openProject(directory: string, navigate = true) {
+    const match = layout.projects.list().find((item) => workspaceKey(item.worktree) === workspaceKey(directory))
+    if (match) {
+      if (navigate) await navigateToProject(match.worktree)
+      return match.worktree
+    }
+
+    const { root, project } = await layout.projects.resolve(directory)
+    await layout.projects.open(directory, { root, project })
+    if (navigate) await navigateToProject(root)
+    return root
   }
 
   const handleDeepLinks = (urls: string[]) => {
     if (!server.isLocal()) return
 
     for (const directory of collectOpenProjectDeepLinks(urls)) {
-      openProject(directory)
+      void openProject(directory)
     }
 
     for (const link of collectNewSessionDeepLinks(urls)) {
-      openProject(link.directory, false)
+      void openProject(link.directory, false)
       const slug = base64Encode(link.directory)
       if (link.prompt) {
         setSessionHandoff(slug, { prompt: link.prompt })
@@ -1355,14 +1363,13 @@ export default function Layout(props: ParentProps) {
   const showEditProjectDialog = (project: LocalProject) => dialog.show(() => <DialogEditProject project={project} />)
 
   async function chooseProject() {
-    function resolve(result: string | string[] | null) {
+    async function resolve(result: string | string[] | null) {
       if (Array.isArray(result)) {
-        for (const directory of result) {
-          openProject(directory, false)
-        }
-        navigateToProject(result[0])
+        const roots = await Promise.all(result.map((directory) => openProject(directory, false)))
+        if (!roots[0]) return
+        await navigateToProject(roots[0])
       } else if (result) {
-        openProject(result)
+        await openProject(result)
       }
     }
 
@@ -1371,11 +1378,11 @@ export default function Layout(props: ParentProps) {
         title: language.t("command.project.open"),
         multiple: true,
       })
-      resolve(result)
+      void resolve(result)
     } else {
       dialog.show(
-        () => <DialogSelectDirectory multiple={true} onSelect={resolve} />,
-        () => resolve(null),
+        () => <DialogSelectDirectory multiple={true} onSelect={(result) => void resolve(result)} />,
+        () => void resolve(null),
       )
     }
   }