diff --git a/tsc/internal/checker/checker.go b/tsc/internal/checker/checker.go
index 2a4ead5003a89..61812da7fbf8b 100644
--- a/tsc/internal/checker/checker.go
+++ b/tsc/internal/checker/checker.go
@@ -18533,6 +18533,12 @@ func (c *Checker) getWidenedTypeOfObjectLiteral(t *Type, context *WideningContex
 	}))
 	// Retain js literal flag through widening
 	result.objectFlags |= t.objectFlags & (ObjectFlagsJSLiteral | ObjectFlagsNonInferrableType)
+	// Remember that this type originates in an object literal so that later subtype checks (e.g. when
+	// computing a common supertype) don't treat it as though it were a "regular" (non-literal) type that
+	// requires target's optional properties to be present (see 'requireOptionalProperties' in relater.go).
+	if isObjectLiteralType(t) {
+		result.objectFlags |= ObjectFlagsWidenedObjectLiteral
+	}
 	// Only cache in child contexts since the root context never widens a particular object literal type more than once
 	if context != nil && context.parent != nil {
 		if context.widenedTypes == nil {
diff --git a/tsc/internal/checker/relater.go b/tsc/internal/checker/relater.go
index 9008420fb7cd1..04eca213bfb41 100644
--- a/tsc/internal/checker/relater.go
+++ b/tsc/internal/checker/relater.go
@@ -4261,7 +4261,7 @@ func (r *Relater) propertiesRelatedTo(source *Type, target *Type, reportErrors b
 			return TernaryFalse
 		}
 	}
-	requireOptionalProperties := (r.relation == r.c.subtypeRelation || r.relation == r.c.strictSubtypeRelation) && !isObjectLiteralType(source) && !r.c.isEmptyArrayLiteralType(source) && !isTupleType(source)
+	requireOptionalProperties := (r.relation == r.c.subtypeRelation || r.relation == r.c.strictSubtypeRelation) && !isObjectLiteralType(source) && source.objectFlags&ObjectFlagsWidenedObjectLiteral == 0 && !r.c.isEmptyArrayLiteralType(source) && !isTupleType(source)
 	unmatchedProperty := r.c.getUnmatchedProperty(source, target, requireOptionalProperties, false /*matchDiscriminantProperties*/)
 	if unmatchedProperty != nil {
 		if reportErrors && r.c.shouldReportUnmatchedPropertyError(source, target) {
diff --git a/tsc/internal/checker/types.go b/tsc/internal/checker/types.go
index 2e8bacbd5df29..177e9cee24d06 100644
--- a/tsc/internal/checker/types.go
+++ b/tsc/internal/checker/types.go
@@ -619,6 +619,7 @@ const (
 	ObjectFlagsCouldContainTypeVariablesComputed          ObjectFlags = 1 << 19 // CouldContainTypeVariables flag has been computed
 	ObjectFlagsCouldContainTypeVariables                  ObjectFlags = 1 << 20 // Type could contain a type variable
 	ObjectFlagsMembersResolved                            ObjectFlags = 1 << 21 // Members have been resolved
+	ObjectFlagsWidenedObjectLiteral                       ObjectFlags = 1 << 31 // Originates in an object literal type that has since been widened
 
 	ObjectFlagsClassOrInterface   = ObjectFlagsClass | ObjectFlagsInterface
 	ObjectFlagsRequiresWidening   = ObjectFlagsContainsWideningType | ObjectFlagsContainsObjectOrArrayLiteral
diff --git a/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.symbols b/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.symbols
new file mode 100644
index 0000000000000..33deb278c9a5c
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.symbols
@@ -0,0 +1,48 @@
+//// [tests/cases/compiler/discriminatedUnionFlatMap.ts] ////
+
+=== discriminatedUnionFlatMap.ts ===
+// https://github.com/microsoft/TypeScript/issues/63776
+
+export type InputOp = { op: "add" } | { op: "remove"; value?: Array<unknown> };
+>InputOp : Symbol(InputOp, Decl(discriminatedUnionFlatMap.ts, 0, 0))
+>op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 2, 23))
+>op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 2, 39))
+>value : Symbol(value, Decl(discriminatedUnionFlatMap.ts, 2, 53))
+>Array : Symbol(Array, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --) ... and 2 more)
+
+export type OutputOp = { op: "add" | "remove" };
+>OutputOp : Symbol(OutputOp, Decl(discriminatedUnionFlatMap.ts, 2, 79))
+>op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 3, 24))
+
+export function f(operations: InputOp[]): OutputOp[] {
+>f : Symbol(f, Decl(discriminatedUnionFlatMap.ts, 3, 48))
+>operations : Symbol(operations, Decl(discriminatedUnionFlatMap.ts, 5, 18))
+>InputOp : Symbol(InputOp, Decl(discriminatedUnionFlatMap.ts, 0, 0))
+>OutputOp : Symbol(OutputOp, Decl(discriminatedUnionFlatMap.ts, 2, 79))
+
+    return operations.flatMap((operation) => {
+>operations.flatMap : Symbol(Array.flatMap, Decl(lib.es2019.array.d.ts, --, --))
+>operations : Symbol(operations, Decl(discriminatedUnionFlatMap.ts, 5, 18))
+>flatMap : Symbol(Array.flatMap, Decl(lib.es2019.array.d.ts, --, --))
+>operation : Symbol(operation, Decl(discriminatedUnionFlatMap.ts, 6, 31))
+
+        if (operation.op === "remove" && operation.value) {
+>operation.op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 2, 23), Decl(discriminatedUnionFlatMap.ts, 2, 39))
+>operation : Symbol(operation, Decl(discriminatedUnionFlatMap.ts, 6, 31))
+>op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 2, 23), Decl(discriminatedUnionFlatMap.ts, 2, 39))
+>operation.value : Symbol(value, Decl(discriminatedUnionFlatMap.ts, 2, 53))
+>operation : Symbol(operation, Decl(discriminatedUnionFlatMap.ts, 6, 31))
+>value : Symbol(value, Decl(discriminatedUnionFlatMap.ts, 2, 53))
+
+            return [].map(() => ({ op: "remove" }));
+>[].map : Symbol(Array.map, Decl(lib.es5.d.ts, --, --))
+>map : Symbol(Array.map, Decl(lib.es5.d.ts, --, --))
+>op : Symbol(op, Decl(discriminatedUnionFlatMap.ts, 8, 34))
+
+        } else {
+            return [operation];
+>operation : Symbol(operation, Decl(discriminatedUnionFlatMap.ts, 6, 31))
+        }
+    });
+}
+
diff --git a/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.types b/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.types
new file mode 100644
index 0000000000000..6794e2294b43f
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/discriminatedUnionFlatMap.types
@@ -0,0 +1,57 @@
+//// [tests/cases/compiler/discriminatedUnionFlatMap.ts] ////
+
+=== discriminatedUnionFlatMap.ts ===
+// https://github.com/microsoft/TypeScript/issues/63776
+
+export type InputOp = { op: "add" } | { op: "remove"; value?: Array<unknown> };
+>InputOp : InputOp
+>op : "add"
+>op : "remove"
+>value : unknown[] | undefined
+
+export type OutputOp = { op: "add" | "remove" };
+>OutputOp : OutputOp
+>op : "add" | "remove"
+
+export function f(operations: InputOp[]): OutputOp[] {
+>f : (operations: InputOp[]) => OutputOp[]
+>operations : InputOp[]
+
+    return operations.flatMap((operation) => {
+>operations.flatMap((operation) => {        if (operation.op === "remove" && operation.value) {            return [].map(() => ({ op: "remove" }));        } else {            return [operation];        }    }) : InputOp[]
+>operations.flatMap : <U, This = undefined>(callback: (this: This, value: InputOp, index: number, array: InputOp[]) => U | readonly U[], thisArg?: This | undefined) => U[]
+>operations : InputOp[]
+>flatMap : <U, This = undefined>(callback: (this: This, value: InputOp, index: number, array: InputOp[]) => U | readonly U[], thisArg?: This | undefined) => U[]
+>(operation) => {        if (operation.op === "remove" && operation.value) {            return [].map(() => ({ op: "remove" }));        } else {            return [operation];        }    } : (this: undefined, operation: InputOp) => InputOp[]
+>operation : InputOp
+
+        if (operation.op === "remove" && operation.value) {
+>operation.op === "remove" && operation.value : false | unknown[] | undefined
+>operation.op === "remove" : boolean
+>operation.op : "add" | "remove"
+>operation : InputOp
+>op : "add" | "remove"
+>"remove" : "remove"
+>operation.value : unknown[] | undefined
+>operation : { op: "remove"; value?: Array<unknown>; }
+>value : unknown[] | undefined
+
+            return [].map(() => ({ op: "remove" }));
+>[].map(() => ({ op: "remove" })) : { op: "remove"; }[]
+>[].map : <U>(callbackfn: (value: never, index: number, array: never[]) => U, thisArg?: any) => U[]
+>[] : never[]
+>map : <U>(callbackfn: (value: never, index: number, array: never[]) => U, thisArg?: any) => U[]
+>() => ({ op: "remove" }) : () => { op: "remove"; }
+>({ op: "remove" }) : { op: "remove"; }
+>{ op: "remove" } : { op: "remove"; }
+>op : "remove"
+>"remove" : "remove"
+
+        } else {
+            return [operation];
+>[operation] : InputOp[]
+>operation : InputOp
+        }
+    });
+}
+
diff --git a/tsc/testdata/tests/cases/compiler/discriminatedUnionFlatMap.ts b/tsc/testdata/tests/cases/compiler/discriminatedUnionFlatMap.ts
new file mode 100644
index 0000000000000..7ff8f6792df52
--- /dev/null
+++ b/tsc/testdata/tests/cases/compiler/discriminatedUnionFlatMap.ts
@@ -0,0 +1,18 @@
+// @strict: true
+// @noEmit: true
+// @lib: es2019
+
+// https://github.com/microsoft/TypeScript/issues/63776
+
+export type InputOp = { op: "add" } | { op: "remove"; value?: Array<unknown> };
+export type OutputOp = { op: "add" | "remove" };
+
+export function f(operations: InputOp[]): OutputOp[] {
+    return operations.flatMap((operation) => {
+        if (operation.op === "remove" && operation.value) {
+            return [].map(() => ({ op: "remove" }));
+        } else {
+            return [operation];
+        }
+    });
+}