diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 90e3a3d2e24de..2a04f34c0de0f 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14709,15 +14709,30 @@ namespace ts {
                     inferFromTypes(source, (<ConditionalType>target).falseType);
                 }
                 else if (target.flags & TypeFlags.UnionOrIntersection) {
+                    // We infer from types that are not naked type variables first so that inferences we
+                    // make from nested naked type variables and given slightly higher priority by virtue
+                    // of being first in the candidates array.
+                    let typeVariableCount = 0;
                     for (const t of (<UnionOrIntersectionType>target).types) {
-                        const savePriority = priority;
-                        // Inferences directly to naked type variables are given lower priority as they are
-                        // less specific. For example, when inferring from Promise<string> to T | Promise<T>,
-                        // we want to infer string for T, not Promise<string> | string.
                         if (getInferenceInfoForType(t)) {
-                            priority |= InferencePriority.NakedTypeVariable;
+                            typeVariableCount++;
+                        }
+                        else {
+                            inferFromTypes(source, t);
+                        }
+                    }
+                    // Inferences directly to naked type variables are given lower priority as they are
+                    // less specific. For example, when inferring from Promise<string> to T | Promise<T>,
+                    // we want to infer string for T, not Promise<string> | string. For intersection types
+                    // we only infer to single naked type variables.
+                    if (target.flags & TypeFlags.Union ? typeVariableCount !== 0 : typeVariableCount === 1) {
+                        const savePriority = priority;
+                        priority |= InferencePriority.NakedTypeVariable;
+                        for (const t of (<UnionOrIntersectionType>target).types) {
+                            if (getInferenceInfoForType(t)) {
+                                inferFromTypes(source, t);
+                            }
                         }
-                        inferFromTypes(source, t);
                         priority = savePriority;
                     }
                 }
diff --git a/tests/baselines/reference/conditionalTypeDoesntSpinForever.types b/tests/baselines/reference/conditionalTypeDoesntSpinForever.types
index 1f4b4a62cd293..d4fe4bf48261b 100644
--- a/tests/baselines/reference/conditionalTypeDoesntSpinForever.types
+++ b/tests/baselines/reference/conditionalTypeDoesntSpinForever.types
@@ -120,9 +120,9 @@ export enum PubSubRecordIsStoredInRedisAsA {
 
         buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString})) as
 >buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString})) as          BuildPubSubRecordType<SO_FAR & {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString}> : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString; }>
->buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString})) : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString; }>
+>buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString})) : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA; }>
 >buildPubSubRecordType : <SO_FAR>(soFar: SO_FAR) => BuildPubSubRecordType<SO_FAR>
->Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString}) : SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString; }
+>Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.jsonEncodedRedisString}) : SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA; }
 >Object.assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
 >Object : ObjectConstructor
 >assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
@@ -144,9 +144,9 @@ export enum PubSubRecordIsStoredInRedisAsA {
 
         buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash})) as
 >buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash})) as          BuildPubSubRecordType<SO_FAR & {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash}> : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.redisHash; }>
->buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash})) : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.redisHash; }>
+>buildPubSubRecordType(Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash})) : BuildPubSubRecordType<SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA; }>
 >buildPubSubRecordType : <SO_FAR>(soFar: SO_FAR) => BuildPubSubRecordType<SO_FAR>
->Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash}) : SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA.redisHash; }
+>Object.assign({}, soFar, {storedAs: PubSubRecordIsStoredInRedisAsA.redisHash}) : SO_FAR & { storedAs: PubSubRecordIsStoredInRedisAsA; }
 >Object.assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
 >Object : ObjectConstructor
 >assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
@@ -337,16 +337,16 @@ export enum PubSubRecordIsStoredInRedisAsA {
 
         buildPubSubRecordType(Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0})) as BuildPubSubRecordType<SO_FAR & {maxMsToWaitBeforePublishing: 0}>,
 >buildPubSubRecordType(Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0})) as BuildPubSubRecordType<SO_FAR & {maxMsToWaitBeforePublishing: 0}> : BuildPubSubRecordType<SO_FAR & { maxMsToWaitBeforePublishing: 0; }>
->buildPubSubRecordType(Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0})) : BuildPubSubRecordType<SO_FAR & { maxMsToWaitBeforePublishing: 0; }>
+>buildPubSubRecordType(Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0})) : BuildPubSubRecordType<SO_FAR & { maxMsToWaitBeforePublishing: number; }>
 >buildPubSubRecordType : <SO_FAR>(soFar: SO_FAR) => BuildPubSubRecordType<SO_FAR>
->Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0}) : SO_FAR & { maxMsToWaitBeforePublishing: 0; }
+>Object.assign({}, soFar, {maxMsToWaitBeforePublishing: 0}) : SO_FAR & { maxMsToWaitBeforePublishing: number; }
 >Object.assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
 >Object : ObjectConstructor
 >assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
 >{} : {}
 >soFar : SO_FAR
->{maxMsToWaitBeforePublishing: 0} : { maxMsToWaitBeforePublishing: 0; }
->maxMsToWaitBeforePublishing : 0
+>{maxMsToWaitBeforePublishing: 0} : { maxMsToWaitBeforePublishing: number; }
+>maxMsToWaitBeforePublishing : number
 >0 : 0
 >maxMsToWaitBeforePublishing : 0
     }
diff --git a/tests/baselines/reference/objectSpread.types b/tests/baselines/reference/objectSpread.types
index e095a4e03bb1c..0ffd5dd20b718 100644
--- a/tests/baselines/reference/objectSpread.types
+++ b/tests/baselines/reference/objectSpread.types
@@ -602,7 +602,7 @@ let exclusive: { id: string, a: number, b: string, c: string, d: boolean } =
 >d : boolean
 
     f({ a: 1, b: 'yes' }, { c: 'no', d: false })
->f({ a: 1, b: 'yes' }, { c: 'no', d: false }) : { a: number; b: string; } & { c: string; d: false; } & { id: string; }
+>f({ a: 1, b: 'yes' }, { c: 'no', d: false }) : { a: number; b: string; } & { c: string; d: boolean; } & { id: string; }
 >f : <T, U>(t: T, u: U) => T & U & { id: string; }
 >{ a: 1, b: 'yes' } : { a: number; b: string; }
 >a : number
diff --git a/tests/baselines/reference/unionAndIntersectionInference1.js b/tests/baselines/reference/unionAndIntersectionInference1.js
index ca9e527d99ed2..fe4d76781d0f4 100644
--- a/tests/baselines/reference/unionAndIntersectionInference1.js
+++ b/tests/baselines/reference/unionAndIntersectionInference1.js
@@ -85,10 +85,16 @@ const createTest = (): ITest => {
 }
 
 declare function f1<T, U>(x: T | U): T | U;
-declare function f2<T, U>(x: T & U): T & U;
+declare function f2<T, U>(x: T, y: U): T | U;
 
 let x1: string = f1('a');
-let x2: string = f2('a');
+let x2: string = f2('a', 'b');
+
+// Repro from #30442
+
+const func = <T>() => {};
+const assign = <T, U>(a: T, b: U) => Object.assign(a, b);
+const res: (() => void) & { func: any } = assign(() => {}, { func });
 
 
 //// [unionAndIntersectionInference1.js]
@@ -134,4 +140,8 @@ const createTest = () => {
     return { name: 'test' };
 };
 let x1 = f1('a');
-let x2 = f2('a');
+let x2 = f2('a', 'b');
+// Repro from #30442
+const func = () => { };
+const assign = (a, b) => Object.assign(a, b);
+const res = assign(() => { }, { func });
diff --git a/tests/baselines/reference/unionAndIntersectionInference1.symbols b/tests/baselines/reference/unionAndIntersectionInference1.symbols
index e866f19daa423..9b4e7244cfd98 100644
--- a/tests/baselines/reference/unionAndIntersectionInference1.symbols
+++ b/tests/baselines/reference/unionAndIntersectionInference1.symbols
@@ -239,12 +239,13 @@ declare function f1<T, U>(x: T | U): T | U;
 >T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 85, 20))
 >U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 85, 22))
 
-declare function f2<T, U>(x: T & U): T & U;
+declare function f2<T, U>(x: T, y: U): T | U;
 >f2 : Symbol(f2, Decl(unionAndIntersectionInference1.ts, 85, 43))
 >T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 86, 20))
 >U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 86, 22))
 >x : Symbol(x, Decl(unionAndIntersectionInference1.ts, 86, 26))
 >T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 86, 20))
+>y : Symbol(y, Decl(unionAndIntersectionInference1.ts, 86, 31))
 >U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 86, 22))
 >T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 86, 20))
 >U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 86, 22))
@@ -253,7 +254,33 @@ let x1: string = f1('a');
 >x1 : Symbol(x1, Decl(unionAndIntersectionInference1.ts, 88, 3))
 >f1 : Symbol(f1, Decl(unionAndIntersectionInference1.ts, 83, 1))
 
-let x2: string = f2('a');
+let x2: string = f2('a', 'b');
 >x2 : Symbol(x2, Decl(unionAndIntersectionInference1.ts, 89, 3))
 >f2 : Symbol(f2, Decl(unionAndIntersectionInference1.ts, 85, 43))
 
+// Repro from #30442
+
+const func = <T>() => {};
+>func : Symbol(func, Decl(unionAndIntersectionInference1.ts, 93, 5))
+>T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 93, 14))
+
+const assign = <T, U>(a: T, b: U) => Object.assign(a, b);
+>assign : Symbol(assign, Decl(unionAndIntersectionInference1.ts, 94, 5))
+>T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 94, 16))
+>U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 94, 18))
+>a : Symbol(a, Decl(unionAndIntersectionInference1.ts, 94, 22))
+>T : Symbol(T, Decl(unionAndIntersectionInference1.ts, 94, 16))
+>b : Symbol(b, Decl(unionAndIntersectionInference1.ts, 94, 27))
+>U : Symbol(U, Decl(unionAndIntersectionInference1.ts, 94, 18))
+>Object.assign : Symbol(ObjectConstructor.assign, Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --))
+>Object : Symbol(Object, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --))
+>assign : Symbol(ObjectConstructor.assign, Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --))
+>a : Symbol(a, Decl(unionAndIntersectionInference1.ts, 94, 22))
+>b : Symbol(b, Decl(unionAndIntersectionInference1.ts, 94, 27))
+
+const res: (() => void) & { func: any } = assign(() => {}, { func });
+>res : Symbol(res, Decl(unionAndIntersectionInference1.ts, 95, 5))
+>func : Symbol(func, Decl(unionAndIntersectionInference1.ts, 95, 27))
+>assign : Symbol(assign, Decl(unionAndIntersectionInference1.ts, 94, 5))
+>func : Symbol(func, Decl(unionAndIntersectionInference1.ts, 95, 60))
+
diff --git a/tests/baselines/reference/unionAndIntersectionInference1.types b/tests/baselines/reference/unionAndIntersectionInference1.types
index 4dddcb8bd0f32..72d60545e6a51 100644
--- a/tests/baselines/reference/unionAndIntersectionInference1.types
+++ b/tests/baselines/reference/unionAndIntersectionInference1.types
@@ -216,9 +216,10 @@ declare function f1<T, U>(x: T | U): T | U;
 >f1 : <T, U>(x: T | U) => T | U
 >x : T | U
 
-declare function f2<T, U>(x: T & U): T & U;
->f2 : <T, U>(x: T & U) => T & U
->x : T & U
+declare function f2<T, U>(x: T, y: U): T | U;
+>f2 : <T, U>(x: T, y: U) => T | U
+>x : T
+>y : U
 
 let x1: string = f1('a');
 >x1 : string
@@ -226,9 +227,37 @@ let x1: string = f1('a');
 >f1 : <T, U>(x: T | U) => T | U
 >'a' : "a"
 
-let x2: string = f2('a');
+let x2: string = f2('a', 'b');
 >x2 : string
->f2('a') : "a"
->f2 : <T, U>(x: T & U) => T & U
+>f2('a', 'b') : "a" | "b"
+>f2 : <T, U>(x: T, y: U) => T | U
 >'a' : "a"
+>'b' : "b"
+
+// Repro from #30442
+
+const func = <T>() => {};
+>func : <T>() => void
+><T>() => {} : <T>() => void
+
+const assign = <T, U>(a: T, b: U) => Object.assign(a, b);
+>assign : <T, U>(a: T, b: U) => T & U
+><T, U>(a: T, b: U) => Object.assign(a, b) : <T, U>(a: T, b: U) => T & U
+>a : T
+>b : U
+>Object.assign(a, b) : T & U
+>Object.assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
+>Object : ObjectConstructor
+>assign : { <T, U>(target: T, source: U): T & U; <T, U, V>(target: T, source1: U, source2: V): T & U & V; <T, U, V, W>(target: T, source1: U, source2: V, source3: W): T & U & V & W; (target: object, ...sources: any[]): any; }
+>a : T
+>b : U
+
+const res: (() => void) & { func: any } = assign(() => {}, { func });
+>res : (() => void) & { func: any; }
+>func : any
+>assign(() => {}, { func }) : (() => void) & { func: <T>() => void; }
+>assign : <T, U>(a: T, b: U) => T & U
+>() => {} : () => void
+>{ func } : { func: <T>() => void; }
+>func : <T>() => void
 
diff --git a/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference1.ts b/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference1.ts
index d4c7d25615e46..18de9c60f2c2f 100644
--- a/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference1.ts
+++ b/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference1.ts
@@ -86,7 +86,13 @@ const createTest = (): ITest => {
 }
 
 declare function f1<T, U>(x: T | U): T | U;
-declare function f2<T, U>(x: T & U): T & U;
+declare function f2<T, U>(x: T, y: U): T | U;
 
 let x1: string = f1('a');
-let x2: string = f2('a');
+let x2: string = f2('a', 'b');
+
+// Repro from #30442
+
+const func = <T>() => {};
+const assign = <T, U>(a: T, b: U) => Object.assign(a, b);
+const res: (() => void) & { func: any } = assign(() => {}, { func });