diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index bfbe961adc7a..0149f1971477 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -69,7 +69,7 @@
     try_expanding_sum_type_to_union, tuple_fallback, make_simplified_union,
     true_only, false_only, erase_to_union_or_bound, function_type,
     callable_type, try_getting_str_literals, custom_special_method,
-    is_literal_type_like,
+    is_literal_type_like, simple_literal_type,
 )
 from mypy.message_registry import ErrorMessage
 import mypy.errorcodes as codes
@@ -3874,26 +3874,43 @@ def visit_conditional_expr(self, e: ConditionalExpr, allow_none_return: bool = F
         if_type = self.analyze_cond_branch(if_map, e.if_expr, context=ctx,
                                            allow_none_return=allow_none_return)
 
+        # we want to keep the narrowest value of if_type for union'ing the branches
+        # however, it would be silly to pass a literal as a type context. Pass the
+        # underlying fallback type instead.
+        if_type_fallback = simple_literal_type(get_proper_type(if_type)) or if_type
+
         # Analyze the right branch using full type context and store the type
         full_context_else_type = self.analyze_cond_branch(else_map, e.else_expr, context=ctx,
                                                           allow_none_return=allow_none_return)
+
         if not mypy.checker.is_valid_inferred_type(if_type):
             # Analyze the right branch disregarding the left branch.
             else_type = full_context_else_type
+            # we want to keep the narrowest value of else_type for union'ing the branches
+            # however, it would be silly to pass a literal as a type context. Pass the
+            # underlying fallback type instead.
+            else_type_fallback = simple_literal_type(get_proper_type(else_type)) or else_type
 
             # If it would make a difference, re-analyze the left
             # branch using the right branch's type as context.
-            if ctx is None or not is_equivalent(else_type, ctx):
+            if ctx is None or not is_equivalent(else_type_fallback, ctx):
                 # TODO: If it's possible that the previous analysis of
                 # the left branch produced errors that are avoided
                 # using this context, suppress those errors.
-                if_type = self.analyze_cond_branch(if_map, e.if_expr, context=else_type,
+                if_type = self.analyze_cond_branch(if_map, e.if_expr, context=else_type_fallback,
                                                    allow_none_return=allow_none_return)
 
+        elif if_type_fallback == ctx:
+            # There is no point re-running the analysis if if_type is equal to ctx.
+            # That would  be an exact duplicate of the work we just did.
+            # This optimization is particularly important to avoid exponential blowup with nested
+            # if/else expressions: https://github.com/python/mypy/issues/9591
+            # TODO: would checking for is_proper_subtype also work and cover more cases?
+            else_type = full_context_else_type
         else:
             # Analyze the right branch in the context of the left
             # branch's type.
-            else_type = self.analyze_cond_branch(else_map, e.else_expr, context=if_type,
+            else_type = self.analyze_cond_branch(else_map, e.else_expr, context=if_type_fallback,
                                                  allow_none_return=allow_none_return)
 
         # Only create a union type if the type context is a union, to be mostly
diff --git a/mypy/typeops.py b/mypy/typeops.py
index e8171e2e85ab..22ca0b6ec2fe 100644
--- a/mypy/typeops.py
+++ b/mypy/typeops.py
@@ -318,7 +318,7 @@ def simple_literal_value_key(t: ProperType) -> Optional[Tuple[str, ...]]:
     return None
 
 
-def simple_literal_type(t: ProperType) -> Optional[Instance]:
+def simple_literal_type(t: Optional[ProperType]) -> Optional[Instance]:
     """Extract the underlying fallback Instance type for a simple Literal"""
     if isinstance(t, Instance) and t.last_known_value is not None:
         t = t.last_known_value