diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index ae1ded9d0d8df..5002819645ff7 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -12313,7 +12313,7 @@ namespace ts {
             return getReducedType(getApparentType(getReducedType(type)));
         }
 
-        function createUnionOrIntersectionProperty(containingType: UnionOrIntersectionType, name: __String, skipObjectFunctionPropertyAugment?: boolean): Symbol | undefined {
+        function createUnionOrIntersectionProperty(containingType: UnionOrIntersectionType, name: __String, skipObjectFunctionPropertyAugment?: boolean, fromIsDiscriminantProperty?: boolean | undefined): Symbol | undefined {
             let singleProp: Symbol | undefined;
             let propSet: ESMap<SymbolId, Symbol> | undefined;
             let indexTypes: Type[] | undefined;
@@ -12438,7 +12438,7 @@ namespace ts {
                 else if (type !== firstType) {
                     checkFlags |= CheckFlags.HasNonUniformType;
                 }
-                if (isLiteralType(type) || isPatternLiteralType(type) || type === uniqueLiteralType) {
+                if ((isLiteralType(type) && (!fromIsDiscriminantProperty || !(type.flags & TypeFlags.Boolean && type.flags & TypeFlags.Union))) || isPatternLiteralType(type) || type === uniqueLiteralType) {
                     checkFlags |= CheckFlags.HasLiteralType;
                 }
                 if (type.flags & TypeFlags.Never && type !== uniqueLiteralType) {
@@ -12481,11 +12481,11 @@ namespace ts {
         // constituents, in which case the isPartial flag is set when the containing type is union type. We need
         // these partial properties when identifying discriminant properties, but otherwise they are filtered out
         // and do not appear to be present in the union type.
-        function getUnionOrIntersectionProperty(type: UnionOrIntersectionType, name: __String, skipObjectFunctionPropertyAugment?: boolean): Symbol | undefined {
+        function getUnionOrIntersectionProperty(type: UnionOrIntersectionType, name: __String, skipObjectFunctionPropertyAugment?: boolean, fromIsDiscriminantProperty?: boolean | undefined): Symbol | undefined {
             let property = type.propertyCacheWithoutObjectFunctionPropertyAugment?.get(name) ||
                 !skipObjectFunctionPropertyAugment ? type.propertyCache?.get(name) : undefined;
             if (!property) {
-                property = createUnionOrIntersectionProperty(type, name, skipObjectFunctionPropertyAugment);
+                property = createUnionOrIntersectionProperty(type, name, skipObjectFunctionPropertyAugment, fromIsDiscriminantProperty);
                 if (property) {
                     const properties = skipObjectFunctionPropertyAugment ?
                         type.propertyCacheWithoutObjectFunctionPropertyAugment ||= createSymbolTable() :
@@ -23219,7 +23219,7 @@ namespace ts {
 
         function isDiscriminantProperty(type: Type | undefined, name: __String) {
             if (type && type.flags & TypeFlags.Union) {
-                const prop = getUnionOrIntersectionProperty(type as UnionType, name);
+                const prop = getUnionOrIntersectionProperty(type as UnionType, name, /* skipObjectFunctionPropertyAugment */ undefined, /* fromIsDiscriminantProperty */ true);
                 if (prop && getCheckFlags(prop) & CheckFlags.SyntheticProperty) {
                     if ((prop as TransientSymbol).isDiscriminantProperty === undefined) {
                         (prop as TransientSymbol).isDiscriminantProperty =
diff --git a/tests/baselines/reference/_44856.js b/tests/baselines/reference/_44856.js
new file mode 100644
index 0000000000000..298533a275687
--- /dev/null
+++ b/tests/baselines/reference/_44856.js
@@ -0,0 +1,76 @@
+//// [_44856.ts]
+// The expected rule for properties of union type (|) is  
+// (1) must contain all required properties of at least one union member
+// (2) may contain additional properties that belong to any union member
+
+{
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: 1}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+}
+
+{
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: boolean};
+    type A4 = {a: string; b: number; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+    }
+  }
+  
+  {
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: boolean};
+    type A4 = {a: string; b: boolean; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+    }
+  }
+
+
+//// [_44856.js]
+// The expected rule for properties of union type (|) is  
+// (1) must contain all required properties of at least one union member
+// (2) may contain additional properties that belong to any union member
+{
+    {
+        // THIS IS THE UNEXPECTED OUTLIER
+        var b = { a: '', b: '', c: 1 }; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+}
+{
+    {
+        // THIS IS THE UNEXPECTED OUTLIER
+        var b = { a: '', b: '', c: true }; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+        // BEHAVING AS EXPECTED
+        var b = { a: '', b: '', c: true }; // ✔ assignments allow extra props of other union types
+    }
+}
+{
+    {
+        // THIS IS THE UNEXPECTED OUTLIER
+        var b = { a: '', b: '', c: true }; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+        // BEHAVING AS EXPECTED
+        var b = { a: '', b: '', c: true }; // ✔ assignments allow extra props of other union types
+    }
+}
diff --git a/tests/baselines/reference/_44856.symbols b/tests/baselines/reference/_44856.symbols
new file mode 100644
index 0000000000000..2da24884770dc
--- /dev/null
+++ b/tests/baselines/reference/_44856.symbols
@@ -0,0 +1,111 @@
+=== tests/cases/compiler/_44856.ts ===
+// The expected rule for properties of union type (|) is  
+// (1) must contain all required properties of at least one union member
+// (2) may contain additional properties that belong to any union member
+
+{
+    type A2 = {a: string; b: string};
+>A2 : Symbol(A2, Decl(_44856.ts, 4, 1))
+>a : Symbol(a, Decl(_44856.ts, 5, 15))
+>b : Symbol(b, Decl(_44856.ts, 5, 25))
+
+    type A3 = {a: string; b: boolean; c: number};
+>A3 : Symbol(A3, Decl(_44856.ts, 5, 37))
+>a : Symbol(a, Decl(_44856.ts, 6, 15))
+>b : Symbol(b, Decl(_44856.ts, 6, 25))
+>c : Symbol(c, Decl(_44856.ts, 6, 37))
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: 1}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : Symbol(b, Decl(_44856.ts, 10, 11))
+>A2 : Symbol(A2, Decl(_44856.ts, 4, 1))
+>A3 : Symbol(A3, Decl(_44856.ts, 5, 37))
+>a : Symbol(a, Decl(_44856.ts, 10, 24))
+>b : Symbol(b, Decl(_44856.ts, 10, 30))
+>c : Symbol(c, Decl(_44856.ts, 10, 37))
+    }
+}
+
+{
+    type A2 = {a: string; b: string};
+>A2 : Symbol(A2, Decl(_44856.ts, 14, 1))
+>a : Symbol(a, Decl(_44856.ts, 15, 15))
+>b : Symbol(b, Decl(_44856.ts, 15, 25))
+
+    type A3 = {a: string; b: boolean; c: boolean};
+>A3 : Symbol(A3, Decl(_44856.ts, 15, 37))
+>a : Symbol(a, Decl(_44856.ts, 16, 15))
+>b : Symbol(b, Decl(_44856.ts, 16, 25))
+>c : Symbol(c, Decl(_44856.ts, 16, 37))
+
+    type A4 = {a: string; b: number; c: number};
+>A4 : Symbol(A4, Decl(_44856.ts, 16, 50))
+>a : Symbol(a, Decl(_44856.ts, 17, 15))
+>b : Symbol(b, Decl(_44856.ts, 17, 25))
+>c : Symbol(c, Decl(_44856.ts, 17, 36))
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : Symbol(b, Decl(_44856.ts, 21, 11))
+>A2 : Symbol(A2, Decl(_44856.ts, 14, 1))
+>A3 : Symbol(A3, Decl(_44856.ts, 15, 37))
+>a : Symbol(a, Decl(_44856.ts, 21, 24))
+>b : Symbol(b, Decl(_44856.ts, 21, 30))
+>c : Symbol(c, Decl(_44856.ts, 21, 37))
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+>b : Symbol(b, Decl(_44856.ts, 25, 11))
+>A2 : Symbol(A2, Decl(_44856.ts, 14, 1))
+>A3 : Symbol(A3, Decl(_44856.ts, 15, 37))
+>A4 : Symbol(A4, Decl(_44856.ts, 16, 50))
+>a : Symbol(a, Decl(_44856.ts, 25, 27))
+>b : Symbol(b, Decl(_44856.ts, 25, 33))
+>c : Symbol(c, Decl(_44856.ts, 25, 40))
+    }
+  }
+  
+  {
+    type A2 = {a: string; b: string};
+>A2 : Symbol(A2, Decl(_44856.ts, 29, 3))
+>a : Symbol(a, Decl(_44856.ts, 30, 15))
+>b : Symbol(b, Decl(_44856.ts, 30, 25))
+
+    type A3 = {a: string; b: boolean; c: boolean};
+>A3 : Symbol(A3, Decl(_44856.ts, 30, 37))
+>a : Symbol(a, Decl(_44856.ts, 31, 15))
+>b : Symbol(b, Decl(_44856.ts, 31, 25))
+>c : Symbol(c, Decl(_44856.ts, 31, 37))
+
+    type A4 = {a: string; b: boolean; c: number};
+>A4 : Symbol(A4, Decl(_44856.ts, 31, 50))
+>a : Symbol(a, Decl(_44856.ts, 32, 15))
+>b : Symbol(b, Decl(_44856.ts, 32, 25))
+>c : Symbol(c, Decl(_44856.ts, 32, 37))
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : Symbol(b, Decl(_44856.ts, 36, 11))
+>A2 : Symbol(A2, Decl(_44856.ts, 29, 3))
+>A3 : Symbol(A3, Decl(_44856.ts, 30, 37))
+>a : Symbol(a, Decl(_44856.ts, 36, 24))
+>b : Symbol(b, Decl(_44856.ts, 36, 30))
+>c : Symbol(c, Decl(_44856.ts, 36, 37))
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+>b : Symbol(b, Decl(_44856.ts, 40, 11))
+>A2 : Symbol(A2, Decl(_44856.ts, 29, 3))
+>A3 : Symbol(A3, Decl(_44856.ts, 30, 37))
+>A4 : Symbol(A4, Decl(_44856.ts, 31, 50))
+>a : Symbol(a, Decl(_44856.ts, 40, 27))
+>b : Symbol(b, Decl(_44856.ts, 40, 33))
+>c : Symbol(c, Decl(_44856.ts, 40, 40))
+    }
+  }
+
diff --git a/tests/baselines/reference/_44856.types b/tests/baselines/reference/_44856.types
new file mode 100644
index 0000000000000..d43944069c0a1
--- /dev/null
+++ b/tests/baselines/reference/_44856.types
@@ -0,0 +1,119 @@
+=== tests/cases/compiler/_44856.ts ===
+// The expected rule for properties of union type (|) is  
+// (1) must contain all required properties of at least one union member
+// (2) may contain additional properties that belong to any union member
+
+{
+    type A2 = {a: string; b: string};
+>A2 : { a: string; b: string; }
+>a : string
+>b : string
+
+    type A3 = {a: string; b: boolean; c: number};
+>A3 : { a: string; b: boolean; c: number; }
+>a : string
+>b : boolean
+>c : number
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: 1}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : { a: string; b: string; } | { a: string; b: boolean; c: number; }
+>{a: '', b: '', c: 1} : { a: string; b: string; c: number; }
+>a : string
+>'' : ""
+>b : string
+>'' : ""
+>c : number
+>1 : 1
+    }
+}
+
+{
+    type A2 = {a: string; b: string};
+>A2 : { a: string; b: string; }
+>a : string
+>b : string
+
+    type A3 = {a: string; b: boolean; c: boolean};
+>A3 : { a: string; b: boolean; c: boolean; }
+>a : string
+>b : boolean
+>c : boolean
+
+    type A4 = {a: string; b: number; c: number};
+>A4 : { a: string; b: number; c: number; }
+>a : string
+>b : number
+>c : number
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : { a: string; b: string; } | { a: string; b: boolean; c: boolean; }
+>{a: '', b: '', c: true} : { a: string; b: string; c: true; }
+>a : string
+>'' : ""
+>b : string
+>'' : ""
+>c : true
+>true : true
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+>b : { a: string; b: string; } | { a: string; b: boolean; c: boolean; } | { a: string; b: number; c: number; }
+>{a: '', b: '', c: true} : { a: string; b: string; c: true; }
+>a : string
+>'' : ""
+>b : string
+>'' : ""
+>c : true
+>true : true
+    }
+  }
+  
+  {
+    type A2 = {a: string; b: string};
+>A2 : { a: string; b: string; }
+>a : string
+>b : string
+
+    type A3 = {a: string; b: boolean; c: boolean};
+>A3 : { a: string; b: boolean; c: boolean; }
+>a : string
+>b : boolean
+>c : boolean
+
+    type A4 = {a: string; b: boolean; c: number};
+>A4 : { a: string; b: boolean; c: number; }
+>a : string
+>b : boolean
+>c : number
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+>b : { a: string; b: string; } | { a: string; b: boolean; c: boolean; }
+>{a: '', b: '', c: true} : { a: string; b: string; c: true; }
+>a : string
+>'' : ""
+>b : string
+>'' : ""
+>c : true
+>true : true
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+>b : { a: string; b: string; } | { a: string; b: boolean; c: boolean; } | { a: string; b: boolean; c: number; }
+>{a: '', b: '', c: true} : { a: string; b: string; c: true; }
+>a : string
+>'' : ""
+>b : string
+>'' : ""
+>c : true
+>true : true
+    }
+  }
+
diff --git a/tests/cases/compiler/_44856.ts b/tests/cases/compiler/_44856.ts
new file mode 100644
index 0000000000000..f31663b2a2b5b
--- /dev/null
+++ b/tests/cases/compiler/_44856.ts
@@ -0,0 +1,43 @@
+// The expected rule for properties of union type (|) is  
+// (1) must contain all required properties of at least one union member
+// (2) may contain additional properties that belong to any union member
+
+{
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: 1}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+}
+
+{
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: boolean};
+    type A4 = {a: string; b: number; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+    }
+  }
+  
+  {
+    type A2 = {a: string; b: string};
+    type A3 = {a: string; b: boolean; c: boolean};
+    type A4 = {a: string; b: boolean; c: number};
+  
+    {
+      // THIS IS THE UNEXPECTED OUTLIER
+      const b: A2|A3 = {a: '', b: '', c: true}; // ❌ assignment strictly checked, extra prop from A3 not allowed
+    }
+    {
+      // BEHAVING AS EXPECTED
+      const b: A2|A3|A4 = {a: '', b: '', c: true}; // ✔ assignments allow extra props of other union types
+    }
+  }