diff --git a/packages/desktop/src/main/shell-env.test.ts b/packages/desktop/src/main/shell-env.test.ts
index e71708ad0491..a4d05bce762a 100644
--- a/packages/desktop/src/main/shell-env.test.ts
+++ b/packages/desktop/src/main/shell-env.test.ts
@@ -1,6 +1,6 @@
 import { describe, expect, test } from "bun:test"
 
-import { isNushell, mergeShellEnv, parseShellEnv, resolveUserShell } from "./shell-env"
+import { isNushell, loadShellEnv, mergeShellEnv, parseShellEnv, resolveUserShell } from "./shell-env"
 
 describe("shell env", () => {
   test("parseShellEnv supports null-delimited pairs", () => {
@@ -47,4 +47,16 @@ describe("shell env", () => {
     expect(isNushell("C:\\Program Files\\nu.exe")).toBe(true)
     expect(isNushell("/bin/zsh")).toBe(false)
   })
+
+  test("loadShellEnv falls back to login shell after interactive timeout", () => {
+    const modes: string[] = []
+    const env = loadShellEnv("/bin/zsh", { log() {} }, (_shell, mode) => {
+      modes.push(mode)
+      if (mode === "-il") return { type: "Timeout" }
+      return { type: "Loaded", value: { PATH: "/usr/local/bin" } }
+    })
+
+    expect(modes).toEqual(["-il", "-l"])
+    expect(env?.PATH).toBe("/usr/local/bin")
+  })
 })
diff --git a/packages/desktop/src/main/shell-env.ts b/packages/desktop/src/main/shell-env.ts
index 082ed5e930db..35553e037008 100644
--- a/packages/desktop/src/main/shell-env.ts
+++ b/packages/desktop/src/main/shell-env.ts
@@ -67,23 +67,22 @@ export function isNushell(shell: string) {
   return name === "nu" || name === "nu.exe" || raw.endsWith("\\nu.exe")
 }
 
-export function loadShellEnv(shell: string, logger: ShellEnvLogger) {
+export function loadShellEnv(shell: string, logger: ShellEnvLogger, probeShell = probe) {
   if (isNushell(shell)) {
     logger.log(`[server] Skipping shell env probe for nushell: ${shell}`)
     return null
   }
 
-  const interactive = probe(shell, "-il")
+  const interactive = probeShell(shell, "-il")
   if (interactive.type === "Loaded") {
     logger.log(`[server] Loaded shell environment with -il (${Object.keys(interactive.value).length} vars)`)
     return interactive.value
   }
   if (interactive.type === "Timeout") {
-    logger.log(`[server] Interactive shell env probe timed out: ${shell}`)
-    return null
+    logger.log(`[server] Interactive shell env probe timed out, retrying with -l: ${shell}`)
   }
 
-  const login = probe(shell, "-l")
+  const login = probeShell(shell, "-l")
   if (login.type === "Loaded") {
     logger.log(`[server] Loaded shell environment with -l (${Object.keys(login.value).length} vars)`)
     return login.value