diff --git a/packages/pyright-internal/src/analyzer/constraintSolver.ts b/packages/pyright-internal/src/analyzer/constraintSolver.ts
index 14ef720fafbe..95add04e952c 100644
--- a/packages/pyright-internal/src/analyzer/constraintSolver.ts
+++ b/packages/pyright-internal/src/analyzer/constraintSolver.ts
@@ -55,6 +55,7 @@ import {
     isEffectivelyInstantiable,
     isPartlyUnknown,
     mapSubtypes,
+    sortTypes,
     specializeTupleClass,
     specializeWithDefaultTypeArgs,
     transformExpectedType,
@@ -1090,7 +1091,7 @@ export function populateTypeVarContextBasedOnExpectedType(
                 if (isUnion(synthTypeVar)) {
                     let foundSynthTypeVar: TypeVarType | undefined;
 
-                    synthTypeVar.subtypes.forEach((subtype) => {
+                    sortTypes(synthTypeVar.subtypes).forEach((subtype) => {
                         if (
                             isTypeVar(subtype) &&
                             subtype.details.isSynthesized &&
diff --git a/packages/pyright-internal/src/analyzer/typeEvaluator.ts b/packages/pyright-internal/src/analyzer/typeEvaluator.ts
index cf78943cbf0c..543b35133d35 100644
--- a/packages/pyright-internal/src/analyzer/typeEvaluator.ts
+++ b/packages/pyright-internal/src/analyzer/typeEvaluator.ts
@@ -3762,6 +3762,7 @@ export function createTypeEvaluator(importLookup: ImportLookup, evaluatorOptions
         type: Type,
         conditionFilter: TypeCondition[] | undefined,
         callback: (expandedSubtype: Type, unexpandedSubtype: Type, isLastIteration: boolean) => Type | undefined,
+        sortSubtypes = false,
         recursionCount = 0
     ): Type {
         const newSubtypes: Type[] = [];
@@ -3772,42 +3773,47 @@ export function createTypeEvaluator(importLookup: ImportLookup, evaluatorOptions
 
             expandedType = transformPossibleRecursiveTypeAlias(expandedType);
 
-            doForEachSubtype(expandedType, (subtype, index, allSubtypes) => {
-                if (conditionFilter) {
-                    const filteredType = applyConditionFilterToType(subtype, conditionFilter, recursionCount);
-                    if (!filteredType) {
-                        return undefined;
-                    }
+            doForEachSubtype(
+                expandedType,
+                (subtype, index, allSubtypes) => {
+                    if (conditionFilter) {
+                        const filteredType = applyConditionFilterToType(subtype, conditionFilter, recursionCount);
+                        if (!filteredType) {
+                            return undefined;
+                        }
 
-                    subtype = filteredType;
-                }
+                        subtype = filteredType;
+                    }
 
-                let transformedType = callback(
-                    subtype,
-                    unexpandedType,
-                    isLastSubtype && index === allSubtypes.length - 1
-                );
-                if (transformedType !== unexpandedType) {
-                    typeChanged = true;
-                }
-                if (transformedType) {
-                    // Apply the type condition if it's associated with a constrained TypeVar.
-                    const typeCondition = getTypeCondition(subtype)?.filter(
-                        (condition) => condition.isConstrainedTypeVar
+                    let transformedType = callback(
+                        subtype,
+                        unexpandedType,
+                        isLastSubtype && index === allSubtypes.length - 1
                     );
-
-                    if (typeCondition && typeCondition.length > 0) {
-                        transformedType = addConditionToType(transformedType, typeCondition);
+                    if (transformedType !== unexpandedType) {
+                        typeChanged = true;
                     }
+                    if (transformedType) {
+                        // Apply the type condition if it's associated with a constrained TypeVar.
+                        const typeCondition = getTypeCondition(subtype)?.filter(
+                            (condition) => condition.isConstrainedTypeVar
+                        );
 
-                    newSubtypes.push(transformedType);
-                }
-                return undefined;
-            });
+                        if (typeCondition && typeCondition.length > 0) {
+                            transformedType = addConditionToType(transformedType, typeCondition);
+                        }
+
+                        newSubtypes.push(transformedType);
+                    }
+                    return undefined;
+                },
+                sortSubtypes
+            );
         }
 
         if (isUnion(type)) {
-            type.subtypes.forEach((subtype, index) => {
+            const subtypes = sortSubtypes ? sortTypes(type.subtypes) : type.subtypes;
+            subtypes.forEach((subtype, index) => {
                 expandSubtype(subtype, index === type.subtypes.length - 1);
             });
         } else {
@@ -3867,6 +3873,7 @@ export function createTypeEvaluator(importLookup: ImportLookup, evaluatorOptions
                     (expandedSubtype) => {
                         return expandedSubtype;
                     },
+                    /* sortSubtypes */ undefined,
                     recursionCount
                 );
 
@@ -8998,7 +9005,8 @@ export function createTypeEvaluator(importLookup: ImportLookup, evaluatorOptions
                         allowDiagnostics: true,
                     }
                 );
-            }
+            },
+            /* sortSubtypes */ true
         );
 
         // If we ended up with a "Never" type because all code paths returned
diff --git a/packages/pyright-internal/src/analyzer/typeUtils.ts b/packages/pyright-internal/src/analyzer/typeUtils.ts
index 7ec748539497..5bd553737885 100644
--- a/packages/pyright-internal/src/analyzer/typeUtils.ts
+++ b/packages/pyright-internal/src/analyzer/typeUtils.ts
@@ -541,15 +541,19 @@ function compareTypes(a: Type, b: Type, recursionCount = 0): number {
                     return bParam.category - aParam.category;
                 }
 
-                const typeComparison = compareTypes(aParam.type, bParam.type);
+                const typeComparison = compareTypes(
+                    FunctionType.getEffectiveParameterType(a, i),
+                    FunctionType.getEffectiveParameterType(bFunc, i)
+                );
+
                 if (typeComparison !== 0) {
                     return typeComparison;
                 }
             }
 
             const returnTypeComparison = compareTypes(
-                a.details.declaredReturnType ?? UnknownType.create(),
-                bFunc.details.declaredReturnType ?? UnknownType.create()
+                FunctionType.getSpecializedReturnType(a) ?? UnknownType.create(),
+                FunctionType.getSpecializedReturnType(bFunc) ?? UnknownType.create()
             );
 
             if (returnTypeComparison !== 0) {
diff --git a/packages/pyright-internal/src/tests/samples/assignment12.py b/packages/pyright-internal/src/tests/samples/assignment12.py
index f823d4fa8f05..ec7d8004c9eb 100644
--- a/packages/pyright-internal/src/tests/samples/assignment12.py
+++ b/packages/pyright-internal/src/tests/samples/assignment12.py
@@ -13,8 +13,8 @@ def a_test(x: int):
 
 def b_test(x: int | str):
     u = x.upper()  # type: ignore
-    reveal_type(u, expected_text="Unknown | str")
+    reveal_type(u, expected_text="str | Unknown")
 
     # This should generate an error if reportUnknownVariableType is enabled.
     y: str = u
-    reveal_type(y, expected_text="Unknown | str")
+    reveal_type(y, expected_text="str | Unknown")
diff --git a/packages/pyright-internal/src/tests/samples/call11.py b/packages/pyright-internal/src/tests/samples/call11.py
index c1af3c803078..5f73ff45dab7 100644
--- a/packages/pyright-internal/src/tests/samples/call11.py
+++ b/packages/pyright-internal/src/tests/samples/call11.py
@@ -41,4 +41,4 @@ def func() -> Either[int, str]:
 
 
 result = func().map_left(lambda lv: lv + 1).map_right(lambda rv: rv + "a")
-reveal_type(result, expected_text="Left[int] | Right[str]")
+reveal_type(result, expected_text="Right[str] | Left[int]")
diff --git a/packages/pyright-internal/src/tests/samples/recursiveTypeAlias8.py b/packages/pyright-internal/src/tests/samples/recursiveTypeAlias8.py
index bf410c9ee371..17e71927ab30 100644
--- a/packages/pyright-internal/src/tests/samples/recursiveTypeAlias8.py
+++ b/packages/pyright-internal/src/tests/samples/recursiveTypeAlias8.py
@@ -31,8 +31,8 @@ class ClassD(TypedDict):
 def foo(a: CorD):
     reveal_type(a, expected_text="ClassC | ClassD")
     options = a.get("options", [])
-    reveal_type(options, expected_text="Any | list[Any] | list[ClassC | ClassD]")
+    reveal_type(options, expected_text="list[ClassC | ClassD] | Any | list[Any]")
 
     for option in options:
-        reveal_type(option, expected_text="Any | ClassC | ClassD")
-        reveal_type(option["type"], expected_text="Any | int")
+        reveal_type(option, expected_text="ClassC | ClassD | Any")
+        reveal_type(option["type"], expected_text="int | Any")