diff --git a/packages/app/src/components/directory-picker-domain.test.ts b/packages/app/src/components/directory-picker-domain.test.ts
index d7d4bf37cb7..8999062656e 100644
--- a/packages/app/src/components/directory-picker-domain.test.ts
+++ b/packages/app/src/components/directory-picker-domain.test.ts
@@ -15,6 +15,8 @@ import {
   treePathWithin,
   currentPickerSuggestions,
   displayPickerPath,
+  pickerParent,
+  pickerRoot,
 } from "./directory-picker-domain"
 
 test("maps server directory entries into Pierre paths", () => {
@@ -96,6 +98,13 @@ test("displays paths using the selected server path format", () => {
   expect(displayPickerPath("/home/luke/repos", "~/repos", "/home/luke")).toBe("~/repos")
 })
 
+test("treats the server share prefix as the UNC root", () => {
+  expect(pickerRoot("//Server/Share/repo/src")).toBe("//Server/Share")
+  expect(pickerRoot("\\\\Server\\Share\\repo\\src")).toBe("//Server/Share")
+  expect(pickerParent("//Server/Share")).toBe("//Server/Share")
+  expect(pickerParent("//Server/Share/repo")).toBe("//Server/Share")
+})
+
 test("exposes autocomplete results only for their source query", () => {
   const result = { query: "/repo/src", items: ["/repo/src/index.ts"] }
   expect(currentPickerSuggestions(result, "/repo/src")).toEqual(result.items)
diff --git a/packages/app/src/components/directory-picker-domain.ts b/packages/app/src/components/directory-picker-domain.ts
index 6826a49788d..27b8b46641a 100644
--- a/packages/app/src/components/directory-picker-domain.ts
+++ b/packages/app/src/components/directory-picker-domain.ts
@@ -207,7 +207,11 @@ export function joinPickerPath(base: string | undefined, relative: string) {
 
 export function pickerRoot(input: string) {
   const value = normalizePickerDrive(input)
-  if (value.startsWith("//")) return "//"
+  if (value.startsWith("//")) {
+    const [server, share] = value.slice(2).split("/")
+    if (server && share) return `//${server}/${share}`
+    return "//"
+  }
   if (value.startsWith("/")) return "/"
   if (/^[A-Za-z]:\//.test(value)) return value.slice(0, 3)
   return ""
@@ -215,8 +219,11 @@ export function pickerRoot(input: string) {
 
 export function pickerParent(input: string) {
   const value = trimPickerPath(input)
+  const root = pickerRoot(value)
+  if (value === root) return value
   if (value === "/" || value === "//" || /^[A-Za-z]:\/$/.test(value)) return value
   const index = value.lastIndexOf("/")
+  if (index < root.length) return root
   if (index <= 0) return "/"
   if (index === 2 && /^[A-Za-z]:/.test(value)) return value.slice(0, 3)
   return value.slice(0, index)