diff --git a/tests/lean/run/305.lean b/tests/lean/run/305.lean
new file mode 100644
index 0000000000..f82d2f257d
--- /dev/null
+++ b/tests/lean/run/305.lean
@@ -0,0 +1,67 @@
+def Unit.longName (f : Unit) : String := ""
+
+inductive Cmd
+  | init
+    (name    : String)
+    (subCmds : Array Cmd)
+    (flags   : Array Unit)
+
+open Inhabited in
+instance : Inhabited Cmd where
+  default := Cmd.init default default default
+
+namespace Cmd
+  def name    : Cmd → String        | init v _ _ => v
+  def subCmds : Cmd → Array Cmd     | init _ v _ => v
+  def flags   : Cmd → Array Unit    | init _ _ v => v
+
+  def subCmd? (c : Cmd) (name : String)     : Option Cmd  := c.subCmds.find? (·.name = name)
+  def flag?   (c : Cmd) (longName : String) : Option Unit := c.flags.find? (·.longName = longName)
+  def hasFlag (c : Cmd) (longName : String) : Bool := c.flag? longName |>.isSome
+
+  def subCmdByFullName? (c : Cmd) (fullName : Array String) : Option Cmd := do
+    let mut c := c
+    guard <| c.name = fullName.get? 0
+    for subName in fullName[1:] do
+      c ← c.subCmd? subName
+    return c
+end Cmd
+
+structure Flag.Parsed where
+  longName : String
+
+abbrev FullCmdName := Array String
+
+structure Cmd.Parsed where
+  name  : FullCmdName
+  flags : Array Flag.Parsed
+
+namespace Cmd.Parsed
+  def hasFlag (c : Cmd.Parsed) (longName : String) : Bool := false
+end Cmd.Parsed
+
+def readSubCmds : Id FullCmdName := panic! ""
+
+def readArgs : Id (Array Flag.Parsed) := panic! ""
+
+def parse (c : Cmd) : Id Cmd.Parsed := do
+  let cmdName ← readSubCmds
+  let flags ← readArgs
+  let cmd := c.subCmdByFullName? cmdName |>. get!
+  let defaultedFlags : Array Flag.Parsed := #[]
+  -- If we uncomment /-: Cmd.Parsed -/ two lines below or comment the line below, the elaborator stops hanging.
+  let flags := defaultedFlags
+  let parsedCmd /- : Cmd.Parsed -/ := {
+    name           := cmdName,
+    flags          := flags
+  }
+  -- If we remove `∨ cmd.hasFlag "version" ∧ parsedCmd.hasFlag "version"` from the condition below,
+  -- the timeout turns into an error. If we also remove `∧ parsedCmd.hasFlag "help"`, it works fine.
+  -- Error:
+  -- synthesized type class instance is not definitionally equal to expression inferred by typing rules, synthesized
+  -- instDecidableAnd
+  -- inferred
+  -- ?m.4652 flags✝ positionalArgs variableArgs
+  if cmd.hasFlag "help" ∧ parsedCmd.hasFlag "help" ∨ cmd.hasFlag "version" ∧ parsedCmd.hasFlag "version" then
+    return parsedCmd
+  return parsedCmd