diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index febb8ffdad3..bee2e3437a2 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14724,17 +14724,25 @@ 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) {
-                        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;
+                        if (!getInferenceInfoForType(t)) {
+                            inferFromTypes(source, t);
                         }
-                        inferFromTypes(source, t);
-                        priority = savePriority;
                     }
+                    // 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) {
+                        if (getInferenceInfoForType(t)) {
+                            inferFromTypes(source, t);
+                        }
+                    }
+                    priority = savePriority;
                 }
                 else if (source.flags & TypeFlags.Union) {
                     // Source is a union or intersection type, infer from each constituent type