diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index ec544ea0950d0..8e3040d3a3566 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14662,7 +14662,7 @@ namespace ts {
                     inferFromTypes(getTrueTypeFromConditionalType(<ConditionalType>source), getTrueTypeFromConditionalType(<ConditionalType>target));
                     inferFromTypes(getFalseTypeFromConditionalType(<ConditionalType>source), getFalseTypeFromConditionalType(<ConditionalType>target));
                 }
-                else if (target.flags & TypeFlags.Conditional) {
+                else if (target.flags & TypeFlags.Conditional && !contravariant) {
                     inferFromTypes(source, getTrueTypeFromConditionalType(<ConditionalType>target));
                     inferFromTypes(source, getFalseTypeFromConditionalType(<ConditionalType>target));
                 }
diff --git a/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.js b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.js
new file mode 100644
index 0000000000000..e911b405074ca
--- /dev/null
+++ b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.js
@@ -0,0 +1,48 @@
+//// [overloadedConstructorFixesInferencesAppropriately.ts]
+interface Box<T> {
+    v: T;
+}
+
+interface ErrorResult {
+    readonly error: true
+}
+
+interface AsyncLoaderProps<TResult extends {}> {
+    readonly asyncLoad: () => Box<TResult>;
+    readonly children: (result: Exclude<TResult, ErrorResult>) => string;
+}
+
+class AsyncLoader<TResult extends {}> {
+    constructor(props: string, context: any);
+    constructor(props: AsyncLoaderProps<TResult>);
+    constructor(...args: any[]) {}
+}
+
+function load(): Box<{ success: true } | ErrorResult> {
+    return null as any;
+}
+
+new AsyncLoader({
+    asyncLoad: load,
+    children: result => result.success as any,
+}); // should work fine
+
+
+//// [overloadedConstructorFixesInferencesAppropriately.js]
+"use strict";
+var AsyncLoader = /** @class */ (function () {
+    function AsyncLoader() {
+        var args = [];
+        for (var _i = 0; _i < arguments.length; _i++) {
+            args[_i] = arguments[_i];
+        }
+    }
+    return AsyncLoader;
+}());
+function load() {
+    return null;
+}
+new AsyncLoader({
+    asyncLoad: load,
+    children: function (result) { return result.success; }
+}); // should work fine
diff --git a/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.symbols b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.symbols
new file mode 100644
index 0000000000000..dd6bb1909d3fe
--- /dev/null
+++ b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.symbols
@@ -0,0 +1,76 @@
+=== tests/cases/compiler/overloadedConstructorFixesInferencesAppropriately.ts ===
+interface Box<T> {
+>Box : Symbol(Box, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 0))
+>T : Symbol(T, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 14))
+
+    v: T;
+>v : Symbol(Box.v, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 18))
+>T : Symbol(T, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 14))
+}
+
+interface ErrorResult {
+>ErrorResult : Symbol(ErrorResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 2, 1))
+
+    readonly error: true
+>error : Symbol(ErrorResult.error, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 4, 23))
+}
+
+interface AsyncLoaderProps<TResult extends {}> {
+>AsyncLoaderProps : Symbol(AsyncLoaderProps, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 6, 1))
+>TResult : Symbol(TResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 8, 27))
+
+    readonly asyncLoad: () => Box<TResult>;
+>asyncLoad : Symbol(AsyncLoaderProps.asyncLoad, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 8, 48))
+>Box : Symbol(Box, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 0))
+>TResult : Symbol(TResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 8, 27))
+
+    readonly children: (result: Exclude<TResult, ErrorResult>) => string;
+>children : Symbol(AsyncLoaderProps.children, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 9, 43))
+>result : Symbol(result, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 10, 24))
+>Exclude : Symbol(Exclude, Decl(lib.es5.d.ts, --, --))
+>TResult : Symbol(TResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 8, 27))
+>ErrorResult : Symbol(ErrorResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 2, 1))
+}
+
+class AsyncLoader<TResult extends {}> {
+>AsyncLoader : Symbol(AsyncLoader, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 11, 1))
+>TResult : Symbol(TResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 13, 18))
+
+    constructor(props: string, context: any);
+>props : Symbol(props, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 14, 16))
+>context : Symbol(context, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 14, 30))
+
+    constructor(props: AsyncLoaderProps<TResult>);
+>props : Symbol(props, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 15, 16))
+>AsyncLoaderProps : Symbol(AsyncLoaderProps, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 6, 1))
+>TResult : Symbol(TResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 13, 18))
+
+    constructor(...args: any[]) {}
+>args : Symbol(args, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 16, 16))
+}
+
+function load(): Box<{ success: true } | ErrorResult> {
+>load : Symbol(load, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 17, 1))
+>Box : Symbol(Box, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 0, 0))
+>success : Symbol(success, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 19, 22))
+>ErrorResult : Symbol(ErrorResult, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 2, 1))
+
+    return null as any;
+}
+
+new AsyncLoader({
+>AsyncLoader : Symbol(AsyncLoader, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 11, 1))
+
+    asyncLoad: load,
+>asyncLoad : Symbol(asyncLoad, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 23, 17))
+>load : Symbol(load, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 17, 1))
+
+    children: result => result.success as any,
+>children : Symbol(children, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 24, 20))
+>result : Symbol(result, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 25, 13))
+>result.success : Symbol(success, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 19, 22))
+>result : Symbol(result, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 25, 13))
+>success : Symbol(success, Decl(overloadedConstructorFixesInferencesAppropriately.ts, 19, 22))
+
+}); // should work fine
+
diff --git a/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.types b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.types
new file mode 100644
index 0000000000000..a486c5d20828e
--- /dev/null
+++ b/tests/baselines/reference/overloadedConstructorFixesInferencesAppropriately.types
@@ -0,0 +1,65 @@
+=== tests/cases/compiler/overloadedConstructorFixesInferencesAppropriately.ts ===
+interface Box<T> {
+    v: T;
+>v : T
+}
+
+interface ErrorResult {
+    readonly error: true
+>error : true
+>true : true
+}
+
+interface AsyncLoaderProps<TResult extends {}> {
+    readonly asyncLoad: () => Box<TResult>;
+>asyncLoad : () => Box<TResult>
+
+    readonly children: (result: Exclude<TResult, ErrorResult>) => string;
+>children : (result: Exclude<TResult, ErrorResult>) => string
+>result : Exclude<TResult, ErrorResult>
+}
+
+class AsyncLoader<TResult extends {}> {
+>AsyncLoader : AsyncLoader<TResult>
+
+    constructor(props: string, context: any);
+>props : string
+>context : any
+
+    constructor(props: AsyncLoaderProps<TResult>);
+>props : AsyncLoaderProps<TResult>
+
+    constructor(...args: any[]) {}
+>args : any[]
+}
+
+function load(): Box<{ success: true } | ErrorResult> {
+>load : () => Box<ErrorResult | { success: true; }>
+>success : true
+>true : true
+
+    return null as any;
+>null as any : any
+>null : null
+}
+
+new AsyncLoader({
+>new AsyncLoader({    asyncLoad: load,    children: result => result.success as any,}) : AsyncLoader<ErrorResult | { success: true; }>
+>AsyncLoader : typeof AsyncLoader
+>{    asyncLoad: load,    children: result => result.success as any,} : { asyncLoad: () => Box<ErrorResult | { success: true; }>; children: (result: { success: true; }) => any; }
+
+    asyncLoad: load,
+>asyncLoad : () => Box<ErrorResult | { success: true; }>
+>load : () => Box<ErrorResult | { success: true; }>
+
+    children: result => result.success as any,
+>children : (result: { success: true; }) => any
+>result => result.success as any : (result: { success: true; }) => any
+>result : { success: true; }
+>result.success as any : any
+>result.success : true
+>result : { success: true; }
+>success : true
+
+}); // should work fine
+
diff --git a/tests/cases/compiler/overloadedConstructorFixesInferencesAppropriately.ts b/tests/cases/compiler/overloadedConstructorFixesInferencesAppropriately.ts
new file mode 100644
index 0000000000000..029316d31c67a
--- /dev/null
+++ b/tests/cases/compiler/overloadedConstructorFixesInferencesAppropriately.ts
@@ -0,0 +1,28 @@
+// @strict: true
+interface Box<T> {
+    v: T;
+}
+
+interface ErrorResult {
+    readonly error: true
+}
+
+interface AsyncLoaderProps<TResult extends {}> {
+    readonly asyncLoad: () => Box<TResult>;
+    readonly children: (result: Exclude<TResult, ErrorResult>) => string;
+}
+
+class AsyncLoader<TResult extends {}> {
+    constructor(props: string, context: any);
+    constructor(props: AsyncLoaderProps<TResult>);
+    constructor(...args: any[]) {}
+}
+
+function load(): Box<{ success: true } | ErrorResult> {
+    return null as any;
+}
+
+new AsyncLoader({
+    asyncLoad: load,
+    children: result => result.success as any,
+}); // should work fine