diff --git a/tsc/internal/checker/flow.go b/tsc/internal/checker/flow.go
index d08254cc8ef88..e5d6e2fb09ec4 100644
--- a/tsc/internal/checker/flow.go
+++ b/tsc/internal/checker/flow.go
@@ -21,6 +21,11 @@ type FlowType struct {
 	incomplete bool
 }
 
+type literalTypeKey struct {
+	flags TypeFlags
+	value any
+}
+
 func (ft *FlowType) isNil() bool {
 	return ft.t == nil
 }
@@ -880,6 +885,11 @@ func (c *Checker) getNarrowedTypeWorker(t *Type, candidate *Type, assumeTrue boo
 	if t == candidate {
 		return candidate
 	}
+	if !checkDerived {
+		if narrowedType := c.tryNarrowLiteralUnion(t, candidate); narrowedType != nil {
+			return narrowedType
+		}
+	}
 	// We first attempt to filter the current type, narrowing constituents as appropriate and removing
 	// constituents that are unrelated to the candidate.
 	var keyPropertyName string
@@ -913,6 +923,17 @@ func (c *Checker) getNarrowedTypeWorker(t *Type, candidate *Type, assumeTrue boo
 			}
 		} else {
 			mapType = func(t *Type) *Type {
+				tLiteralFlags := t.flags & TypeFlagsLiteral
+				nLiteralFlags := n.flags & TypeFlagsLiteral
+				if tLiteralFlags != 0 && tLiteralFlags == nLiteralFlags && !(t.flags&TypeFlagsEnumLiteral != 0 && n.flags&TypeFlagsEnumLiteral != 0) {
+					if t.AsLiteralType().value == n.AsLiteralType().value {
+						if n.flags&TypeFlagsEnumLiteral != 0 {
+							return n
+						}
+						return t
+					}
+					return c.neverType
+				}
 				switch {
 				case c.isTypeStrictSubtypeOf(t, n):
 					return t
@@ -963,6 +984,23 @@ func (c *Checker) getNarrowedTypeWorker(t *Type, candidate *Type, assumeTrue boo
 	return c.getIntersectionType([]*Type{t, candidate})
 }
 
+func (c *Checker) tryNarrowLiteralUnion(t *Type, candidate *Type) *Type {
+	isNonEnumLiteral := func(t *Type) bool {
+		return t.flags&TypeFlagsLiteral != 0 && t.flags&TypeFlagsEnumLiteral == 0
+	}
+	if !everyType(t, isNonEnumLiteral) || !everyType(candidate, isNonEnumLiteral) {
+		return nil
+	}
+	candidateTypes := make(map[literalTypeKey]struct{})
+	forEachType(candidate, func(t *Type) {
+		candidateTypes[literalTypeKey{flags: t.flags & TypeFlagsLiteral, value: t.AsLiteralType().value}] = struct{}{}
+	})
+	return c.filterType(t, func(t *Type) bool {
+		_, ok := candidateTypes[literalTypeKey{flags: t.flags & TypeFlagsLiteral, value: t.AsLiteralType().value}]
+		return ok
+	})
+}
+
 func (c *Checker) getInstanceType(constructorType *Type) *Type {
 	prototypePropertyType := c.getTypeOfPropertyOfType(constructorType, "prototype")
 	if prototypePropertyType != nil && !IsTypeAny(prototypePropertyType) {
diff --git a/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.js b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.js
new file mode 100644
index 0000000000000..43ae6d32f0bd3
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.js
@@ -0,0 +1,39 @@
+//// [tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts] ////
+
+//// [narrowLiteralUnionByTypePredicate.ts]
+type Source = "a" | "b" | "c" | "d" | 1 | 2 | 3 | 4;
+type Candidate = "b" | "d" | 1 | 3;
+
+declare const source: Source;
+declare function isCandidate(value: Source): value is Candidate;
+
+if (isCandidate(source)) {
+    source;
+}
+
+enum E {
+    A = "a",
+    B = "b",
+}
+
+declare const enumSource: "a" | "b";
+declare function isEnumA(value: "a" | "b"): value is E.A;
+
+if (isEnumA(enumSource)) {
+    const enumA: E.A = enumSource;
+}
+
+
+//// [narrowLiteralUnionByTypePredicate.js]
+"use strict";
+if (isCandidate(source)) {
+    source;
+}
+var E;
+(function (E) {
+    E["A"] = "a";
+    E["B"] = "b";
+})(E || (E = {}));
+if (isEnumA(enumSource)) {
+    const enumA = enumSource;
+}
diff --git a/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.symbols b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.symbols
new file mode 100644
index 0000000000000..570ee92c47fbb
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.symbols
@@ -0,0 +1,59 @@
+//// [tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts] ////
+
+=== narrowLiteralUnionByTypePredicate.ts ===
+type Source = "a" | "b" | "c" | "d" | 1 | 2 | 3 | 4;
+>Source : Symbol(Source, Decl(narrowLiteralUnionByTypePredicate.ts, 0, 0))
+
+type Candidate = "b" | "d" | 1 | 3;
+>Candidate : Symbol(Candidate, Decl(narrowLiteralUnionByTypePredicate.ts, 0, 52))
+
+declare const source: Source;
+>source : Symbol(source, Decl(narrowLiteralUnionByTypePredicate.ts, 3, 13))
+>Source : Symbol(Source, Decl(narrowLiteralUnionByTypePredicate.ts, 0, 0))
+
+declare function isCandidate(value: Source): value is Candidate;
+>isCandidate : Symbol(isCandidate, Decl(narrowLiteralUnionByTypePredicate.ts, 3, 29))
+>value : Symbol(value, Decl(narrowLiteralUnionByTypePredicate.ts, 4, 29))
+>Source : Symbol(Source, Decl(narrowLiteralUnionByTypePredicate.ts, 0, 0))
+>value : Symbol(value, Decl(narrowLiteralUnionByTypePredicate.ts, 4, 29))
+>Candidate : Symbol(Candidate, Decl(narrowLiteralUnionByTypePredicate.ts, 0, 52))
+
+if (isCandidate(source)) {
+>isCandidate : Symbol(isCandidate, Decl(narrowLiteralUnionByTypePredicate.ts, 3, 29))
+>source : Symbol(source, Decl(narrowLiteralUnionByTypePredicate.ts, 3, 13))
+
+    source;
+>source : Symbol(source, Decl(narrowLiteralUnionByTypePredicate.ts, 3, 13))
+}
+
+enum E {
+>E : Symbol(E, Decl(narrowLiteralUnionByTypePredicate.ts, 8, 1))
+
+    A = "a",
+>A : Symbol(E.A, Decl(narrowLiteralUnionByTypePredicate.ts, 10, 8))
+
+    B = "b",
+>B : Symbol(E.B, Decl(narrowLiteralUnionByTypePredicate.ts, 11, 12))
+}
+
+declare const enumSource: "a" | "b";
+>enumSource : Symbol(enumSource, Decl(narrowLiteralUnionByTypePredicate.ts, 15, 13))
+
+declare function isEnumA(value: "a" | "b"): value is E.A;
+>isEnumA : Symbol(isEnumA, Decl(narrowLiteralUnionByTypePredicate.ts, 15, 36))
+>value : Symbol(value, Decl(narrowLiteralUnionByTypePredicate.ts, 16, 25))
+>value : Symbol(value, Decl(narrowLiteralUnionByTypePredicate.ts, 16, 25))
+>E : Symbol(E, Decl(narrowLiteralUnionByTypePredicate.ts, 8, 1))
+>A : Symbol(E.A, Decl(narrowLiteralUnionByTypePredicate.ts, 10, 8))
+
+if (isEnumA(enumSource)) {
+>isEnumA : Symbol(isEnumA, Decl(narrowLiteralUnionByTypePredicate.ts, 15, 36))
+>enumSource : Symbol(enumSource, Decl(narrowLiteralUnionByTypePredicate.ts, 15, 13))
+
+    const enumA: E.A = enumSource;
+>enumA : Symbol(enumA, Decl(narrowLiteralUnionByTypePredicate.ts, 19, 9))
+>E : Symbol(E, Decl(narrowLiteralUnionByTypePredicate.ts, 8, 1))
+>A : Symbol(E.A, Decl(narrowLiteralUnionByTypePredicate.ts, 10, 8))
+>enumSource : Symbol(enumSource, Decl(narrowLiteralUnionByTypePredicate.ts, 15, 13))
+}
+
diff --git a/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.types b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.types
new file mode 100644
index 0000000000000..f8b7188f14618
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/narrowLiteralUnionByTypePredicate.types
@@ -0,0 +1,56 @@
+//// [tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts] ////
+
+=== narrowLiteralUnionByTypePredicate.ts ===
+type Source = "a" | "b" | "c" | "d" | 1 | 2 | 3 | 4;
+>Source : Source
+
+type Candidate = "b" | "d" | 1 | 3;
+>Candidate : Candidate
+
+declare const source: Source;
+>source : Source
+
+declare function isCandidate(value: Source): value is Candidate;
+>isCandidate : (value: Source) => value is Candidate
+>value : Source
+
+if (isCandidate(source)) {
+>isCandidate(source) : boolean
+>isCandidate : (value: Source) => value is Candidate
+>source : Source
+
+    source;
+>source : "b" | "d" | 1 | 3
+}
+
+enum E {
+>E : E
+
+    A = "a",
+>A : E.A
+>"a" : "a"
+
+    B = "b",
+>B : E.B
+>"b" : "b"
+}
+
+declare const enumSource: "a" | "b";
+>enumSource : "a" | "b"
+
+declare function isEnumA(value: "a" | "b"): value is E.A;
+>isEnumA : (value: "a" | "b") => value is E.A
+>value : "a" | "b"
+>E : any
+
+if (isEnumA(enumSource)) {
+>isEnumA(enumSource) : boolean
+>isEnumA : (value: "a" | "b") => value is E.A
+>enumSource : "a" | "b"
+
+    const enumA: E.A = enumSource;
+>enumA : E.A
+>E : any
+>enumSource : E.A
+}
+
diff --git a/tsc/testdata/tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts b/tsc/testdata/tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts
new file mode 100644
index 0000000000000..3bdd49ee38b52
--- /dev/null
+++ b/tsc/testdata/tests/cases/compiler/narrowLiteralUnionByTypePredicate.ts
@@ -0,0 +1,23 @@
+// @strict: true
+
+type Source = "a" | "b" | "c" | "d" | 1 | 2 | 3 | 4;
+type Candidate = "b" | "d" | 1 | 3;
+
+declare const source: Source;
+declare function isCandidate(value: Source): value is Candidate;
+
+if (isCandidate(source)) {
+    source;
+}
+
+enum E {
+    A = "a",
+    B = "b",
+}
+
+declare const enumSource: "a" | "b";
+declare function isEnumA(value: "a" | "b"): value is E.A;
+
+if (isEnumA(enumSource)) {
+    const enumA: E.A = enumSource;
+}