diff --git a/runtime/lua/vim/_system.lua b/runtime/lua/vim/_system.lua
index 947aa5c86f..72de1288b1 100644
--- a/runtime/lua/vim/_system.lua
+++ b/runtime/lua/vim/_system.lua
@@ -245,7 +245,13 @@ local function spawn(cmd, opts, on_exit, on_error)
   local handle, pid_or_err = uv.spawn(cmd, opts, on_exit)
   if not handle then
     on_error()
-    error(('%s: "%s"'):format(pid_or_err, cmd))
+    if opts.cwd and not uv.fs_stat(opts.cwd) then
+      error(("%s (cwd): '%s'"):format(pid_or_err, opts.cwd))
+    elseif vim.fn.executable(cmd) == 0 then
+      error(("%s (cmd): '%s'"):format(pid_or_err, cmd))
+    else
+      error(pid_or_err)
+    end
   end
   return handle, pid_or_err --[[@as integer]]
 end
diff --git a/test/functional/lua/system_spec.lua b/test/functional/lua/system_spec.lua
index 5abd901a9d..52206b7906 100644
--- a/test/functional/lua/system_spec.lua
+++ b/test/functional/lua/system_spec.lua
@@ -55,9 +55,14 @@ describe('vim.system', function()
     describe('(' .. name .. ')', function()
       it('failure modes', function()
         t.matches(
-          'ENOENT%: no such file .*: "non%-existent%-cmd"',
+          "ENOENT%: no such file .* %(cmd%): 'non%-existent%-cmd'",
           t.pcall_err(system, { 'non-existent-cmd', 'arg1', 'arg2' }, { text = true })
         )
+
+        t.matches(
+          "ENOENT%: no such file .* %(cwd%): 'non%-existent%-cwd'",
+          t.pcall_err(system, { 'echo', 'hello' }, { cwd = 'non-existent-cwd', text = true })
+        )
       end)
 
       it('can run simple commands', function()