diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 7b6d49cf8f9c4..e3e6b947bde73 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -18821,7 +18821,8 @@ m2: ${(this.mapper2 as unknown as DebugTypeMapper).__debugToString().split("\n")
                         }
                     }
 
-                    const isPerformingCommonPropertyChecks = relation !== comparableRelation && !(intersectionState & IntersectionState.Target) &&
+                    const isPerformingCommonPropertyChecks = (relation !== comparableRelation || relation === comparableRelation && isLiteralType(source)) &&
+                        !(intersectionState & IntersectionState.Target) &&
                         source.flags & (TypeFlags.Primitive | TypeFlags.Object | TypeFlags.Intersection) && source !== globalObjectType &&
                         target.flags & (TypeFlags.Object | TypeFlags.Intersection) && isWeakType(target) &&
                         (getPropertiesOfType(source).length > 0 || typeHasCallOrConstructSignatures(source));
diff --git a/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.js b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.js
new file mode 100644
index 0000000000000..d9736d75f2d4e
--- /dev/null
+++ b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.js
@@ -0,0 +1,50 @@
+//// [weakTypeAndPrimitiveNarrowing.ts]
+type LiteralsAndWeakTypes = 
+  | 'A'
+  | 'B'
+  | { optional?: true }
+  | { toLowerCase?(): string }
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+
+const g = (arg: LiteralsAndWeakTypes) => {
+    if (arg === 'A') {
+      arg;
+    } else {
+      arg;
+    }
+}
+
+type PrimitivesAndWeakTypes =
+  | string
+  | number
+  | { optional?: true }
+  | { toLowerCase?(): string }
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+
+const h = (arg: PrimitivesAndWeakTypes) => {
+    if (arg === 'A') {
+      arg;
+    } else {
+      arg;
+    }
+}
+
+
+//// [weakTypeAndPrimitiveNarrowing.js]
+"use strict";
+var g = function (arg) {
+    if (arg === 'A') {
+        arg;
+    }
+    else {
+        arg;
+    }
+};
+var h = function (arg) {
+    if (arg === 'A') {
+        arg;
+    }
+    else {
+        arg;
+    }
+};
diff --git a/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.symbols b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.symbols
new file mode 100644
index 0000000000000..0d1f0edab74cf
--- /dev/null
+++ b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.symbols
@@ -0,0 +1,65 @@
+=== tests/cases/compiler/weakTypeAndPrimitiveNarrowing.ts ===
+type LiteralsAndWeakTypes = 
+>LiteralsAndWeakTypes : Symbol(LiteralsAndWeakTypes, Decl(weakTypeAndPrimitiveNarrowing.ts, 0, 0))
+
+  | 'A'
+  | 'B'
+  | { optional?: true }
+>optional : Symbol(optional, Decl(weakTypeAndPrimitiveNarrowing.ts, 3, 5))
+
+  | { toLowerCase?(): string }
+>toLowerCase : Symbol(toLowerCase, Decl(weakTypeAndPrimitiveNarrowing.ts, 4, 5))
+
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+>toUpperCase : Symbol(toUpperCase, Decl(weakTypeAndPrimitiveNarrowing.ts, 5, 5))
+>otherOptionalProp : Symbol(otherOptionalProp, Decl(weakTypeAndPrimitiveNarrowing.ts, 5, 29))
+
+const g = (arg: LiteralsAndWeakTypes) => {
+>g : Symbol(g, Decl(weakTypeAndPrimitiveNarrowing.ts, 7, 5))
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 7, 11))
+>LiteralsAndWeakTypes : Symbol(LiteralsAndWeakTypes, Decl(weakTypeAndPrimitiveNarrowing.ts, 0, 0))
+
+    if (arg === 'A') {
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 7, 11))
+
+      arg;
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 7, 11))
+
+    } else {
+      arg;
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 7, 11))
+    }
+}
+
+type PrimitivesAndWeakTypes =
+>PrimitivesAndWeakTypes : Symbol(PrimitivesAndWeakTypes, Decl(weakTypeAndPrimitiveNarrowing.ts, 13, 1))
+
+  | string
+  | number
+  | { optional?: true }
+>optional : Symbol(optional, Decl(weakTypeAndPrimitiveNarrowing.ts, 18, 5))
+
+  | { toLowerCase?(): string }
+>toLowerCase : Symbol(toLowerCase, Decl(weakTypeAndPrimitiveNarrowing.ts, 19, 5))
+
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+>toUpperCase : Symbol(toUpperCase, Decl(weakTypeAndPrimitiveNarrowing.ts, 20, 5))
+>otherOptionalProp : Symbol(otherOptionalProp, Decl(weakTypeAndPrimitiveNarrowing.ts, 20, 29))
+
+const h = (arg: PrimitivesAndWeakTypes) => {
+>h : Symbol(h, Decl(weakTypeAndPrimitiveNarrowing.ts, 22, 5))
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 22, 11))
+>PrimitivesAndWeakTypes : Symbol(PrimitivesAndWeakTypes, Decl(weakTypeAndPrimitiveNarrowing.ts, 13, 1))
+
+    if (arg === 'A') {
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 22, 11))
+
+      arg;
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 22, 11))
+
+    } else {
+      arg;
+>arg : Symbol(arg, Decl(weakTypeAndPrimitiveNarrowing.ts, 22, 11))
+    }
+}
+
diff --git a/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.types b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.types
new file mode 100644
index 0000000000000..e0db0a93b8d0a
--- /dev/null
+++ b/tests/baselines/reference/weakTypeAndPrimitiveNarrowing.types
@@ -0,0 +1,71 @@
+=== tests/cases/compiler/weakTypeAndPrimitiveNarrowing.ts ===
+type LiteralsAndWeakTypes = 
+>LiteralsAndWeakTypes : { optional?: true | undefined; } | { toLowerCase?(): string; } | { toUpperCase?(): string; otherOptionalProp?: number | undefined; } | "A" | "B"
+
+  | 'A'
+  | 'B'
+  | { optional?: true }
+>optional : true | undefined
+>true : true
+
+  | { toLowerCase?(): string }
+>toLowerCase : (() => string) | undefined
+
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+>toUpperCase : (() => string) | undefined
+>otherOptionalProp : number | undefined
+
+const g = (arg: LiteralsAndWeakTypes) => {
+>g : (arg: LiteralsAndWeakTypes) => void
+>(arg: LiteralsAndWeakTypes) => {    if (arg === 'A') {      arg;    } else {      arg;    }} : (arg: LiteralsAndWeakTypes) => void
+>arg : LiteralsAndWeakTypes
+
+    if (arg === 'A') {
+>arg === 'A' : boolean
+>arg : LiteralsAndWeakTypes
+>'A' : "A"
+
+      arg;
+>arg : { toLowerCase?(): string; } | { toUpperCase?(): string; otherOptionalProp?: number | undefined; } | "A"
+
+    } else {
+      arg;
+>arg : { optional?: true | undefined; } | { toLowerCase?(): string; } | { toUpperCase?(): string; otherOptionalProp?: number | undefined; } | "B"
+    }
+}
+
+type PrimitivesAndWeakTypes =
+>PrimitivesAndWeakTypes : string | number | { optional?: true | undefined; } | { toLowerCase?(): string; } | { toUpperCase?(): string; otherOptionalProp?: number | undefined; }
+
+  | string
+  | number
+  | { optional?: true }
+>optional : true | undefined
+>true : true
+
+  | { toLowerCase?(): string }
+>toLowerCase : (() => string) | undefined
+
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+>toUpperCase : (() => string) | undefined
+>otherOptionalProp : number | undefined
+
+const h = (arg: PrimitivesAndWeakTypes) => {
+>h : (arg: PrimitivesAndWeakTypes) => void
+>(arg: PrimitivesAndWeakTypes) => {    if (arg === 'A') {      arg;    } else {      arg;    }} : (arg: PrimitivesAndWeakTypes) => void
+>arg : PrimitivesAndWeakTypes
+
+    if (arg === 'A') {
+>arg === 'A' : boolean
+>arg : PrimitivesAndWeakTypes
+>'A' : "A"
+
+      arg;
+>arg : "A" | { toLowerCase?(): string; } | { toUpperCase?(): string; otherOptionalProp?: number | undefined; }
+
+    } else {
+      arg;
+>arg : PrimitivesAndWeakTypes
+    }
+}
+
diff --git a/tests/cases/compiler/weakTypeAndPrimitiveNarrowing.ts b/tests/cases/compiler/weakTypeAndPrimitiveNarrowing.ts
new file mode 100644
index 0000000000000..df3d9de530b39
--- /dev/null
+++ b/tests/cases/compiler/weakTypeAndPrimitiveNarrowing.ts
@@ -0,0 +1,31 @@
+// @strict: true
+
+type LiteralsAndWeakTypes = 
+  | 'A'
+  | 'B'
+  | { optional?: true }
+  | { toLowerCase?(): string }
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+
+const g = (arg: LiteralsAndWeakTypes) => {
+    if (arg === 'A') {
+      arg;
+    } else {
+      arg;
+    }
+}
+
+type PrimitivesAndWeakTypes =
+  | string
+  | number
+  | { optional?: true }
+  | { toLowerCase?(): string }
+  | { toUpperCase?(): string, otherOptionalProp?: number };
+
+const h = (arg: PrimitivesAndWeakTypes) => {
+    if (arg === 'A') {
+      arg;
+    } else {
+      arg;
+    }
+}