diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 1ee59b8862bf6..4581ceaf1e263 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14770,17 +14770,25 @@ 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.
+                    for (const t of (<UnionOrIntersectionType>target).types) {
+                        if (!getInferenceInfoForType(t)) {
+                            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.
+                    const savePriority = priority;
+                    priority |= InferencePriority.NakedTypeVariable;
                     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;
+                            inferFromTypes(source, t);
                         }
-                        inferFromTypes(source, t);
-                        priority = savePriority;
                     }
+                    priority = savePriority;
                 }
                 else if (source.flags & TypeFlags.Union) {
                     // Source is a union or intersection type, infer from each constituent type
diff --git a/tests/baselines/reference/unionAndIntersectionInference3.js b/tests/baselines/reference/unionAndIntersectionInference3.js
new file mode 100644
index 0000000000000..4cc0c2f667e59
--- /dev/null
+++ b/tests/baselines/reference/unionAndIntersectionInference3.js
@@ -0,0 +1,12 @@
+//// [unionAndIntersectionInference3.ts]
+// Repro from #30720
+
+type Maybe<T> = T | undefined;
+declare function concatMaybe<T>(...args: (Maybe<T> | Maybe<T>[])[]): T[];
+concatMaybe([1, 2, 3], 4);
+
+
+//// [unionAndIntersectionInference3.js]
+"use strict";
+// Repro from #30720
+concatMaybe([1, 2, 3], 4);
diff --git a/tests/baselines/reference/unionAndIntersectionInference3.symbols b/tests/baselines/reference/unionAndIntersectionInference3.symbols
new file mode 100644
index 0000000000000..be24bc0cc7781
--- /dev/null
+++ b/tests/baselines/reference/unionAndIntersectionInference3.symbols
@@ -0,0 +1,21 @@
+=== tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference3.ts ===
+// Repro from #30720
+
+type Maybe<T> = T | undefined;
+>Maybe : Symbol(Maybe, Decl(unionAndIntersectionInference3.ts, 0, 0))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 2, 11))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 2, 11))
+
+declare function concatMaybe<T>(...args: (Maybe<T> | Maybe<T>[])[]): T[];
+>concatMaybe : Symbol(concatMaybe, Decl(unionAndIntersectionInference3.ts, 2, 30))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 3, 29))
+>args : Symbol(args, Decl(unionAndIntersectionInference3.ts, 3, 32))
+>Maybe : Symbol(Maybe, Decl(unionAndIntersectionInference3.ts, 0, 0))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 3, 29))
+>Maybe : Symbol(Maybe, Decl(unionAndIntersectionInference3.ts, 0, 0))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 3, 29))
+>T : Symbol(T, Decl(unionAndIntersectionInference3.ts, 3, 29))
+
+concatMaybe([1, 2, 3], 4);
+>concatMaybe : Symbol(concatMaybe, Decl(unionAndIntersectionInference3.ts, 2, 30))
+
diff --git a/tests/baselines/reference/unionAndIntersectionInference3.types b/tests/baselines/reference/unionAndIntersectionInference3.types
new file mode 100644
index 0000000000000..8497cb1e5161f
--- /dev/null
+++ b/tests/baselines/reference/unionAndIntersectionInference3.types
@@ -0,0 +1,19 @@
+=== tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference3.ts ===
+// Repro from #30720
+
+type Maybe<T> = T | undefined;
+>Maybe : Maybe<T>
+
+declare function concatMaybe<T>(...args: (Maybe<T> | Maybe<T>[])[]): T[];
+>concatMaybe : <T>(...args: (T | Maybe<T>[] | undefined)[]) => T[]
+>args : (T | Maybe<T>[] | undefined)[]
+
+concatMaybe([1, 2, 3], 4);
+>concatMaybe([1, 2, 3], 4) : number[]
+>concatMaybe : <T>(...args: (T | Maybe<T>[] | undefined)[]) => T[]
+>[1, 2, 3] : number[]
+>1 : 1
+>2 : 2
+>3 : 3
+>4 : 4
+
diff --git a/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference3.ts b/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference3.ts
new file mode 100644
index 0000000000000..aad083a626b26
--- /dev/null
+++ b/tests/cases/conformance/types/typeRelationships/typeInference/unionAndIntersectionInference3.ts
@@ -0,0 +1,7 @@
+// @strict: true
+
+// Repro from #30720
+
+type Maybe<T> = T | undefined;
+declare function concatMaybe<T>(...args: (Maybe<T> | Maybe<T>[])[]): T[];
+concatMaybe([1, 2, 3], 4);