diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 9347329e624b2..7e3d9f253d0f2 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -16350,10 +16350,15 @@ namespace ts {
                         }
                         if (!checkApplicableSignature(node, args, candidate, relation, excludeArgument, /*reportErrors*/ false)) {
                             candidateForArgumentError = candidate;
-                            break;
+                            if (candidates.length > 1) {
+                                break;
+                            }
                         }
                         if (excludeCount === 0) {
                             candidates[candidateIndex] = candidate;
+                            if (candidate === candidateForArgumentError) {
+                                break;
+                            }
                             return candidate;
                         }
                         excludeCount--;
diff --git a/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.errors.txt b/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.errors.txt
index 0fe1e69d0799c..807e73092b26c 100644
--- a/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.errors.txt
+++ b/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.errors.txt
@@ -1,6 +1,6 @@
 tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(2,22): error TS2339: Property 'foo' does not exist on type 'string'.
-tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(3,32): error TS2339: Property 'foo' does not exist on type '""'.
-tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(3,38): error TS2345: Argument of type '1' is not assignable to parameter of type '""'.
+tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(3,32): error TS2339: Property 'foo' does not exist on type 'string'.
+tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(3,38): error TS2345: Argument of type '1' is not assignable to parameter of type 'string'.
 
 
 ==== tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts (3 errors) ====
@@ -10,6 +10,6 @@ tests/cases/compiler/contextualTypingWithFixedTypeParameters1.ts(3,38): error TS
 !!! error TS2339: Property 'foo' does not exist on type 'string'.
     var r9 = f10('', () => (a => a.foo), 1); // error
                                    ~~~
-!!! error TS2339: Property 'foo' does not exist on type '""'.
+!!! error TS2339: Property 'foo' does not exist on type 'string'.
                                          ~
-!!! error TS2345: Argument of type '1' is not assignable to parameter of type '""'.
\ No newline at end of file
+!!! error TS2345: Argument of type '1' is not assignable to parameter of type 'string'.
\ No newline at end of file
diff --git a/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.types b/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.types
index c0100b060889f..84b2077523a9a 100644
--- a/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.types
+++ b/tests/baselines/reference/contextualTypingWithFixedTypeParameters1.types
@@ -28,12 +28,12 @@ var r9 = f10('', () => (a => a.foo), 1); // error
 >f10('', () => (a => a.foo), 1) : any
 >f10 : <T>(x: T, b: () => (a: T) => void, y: T) => T
 >'' : ""
->() => (a => a.foo) : () => (a: "") => any
->(a => a.foo) : (a: "") => any
->a => a.foo : (a: "") => any
->a : ""
+>() => (a => a.foo) : () => (a: string) => any
+>(a => a.foo) : (a: string) => any
+>a => a.foo : (a: string) => any
+>a : string
 >a.foo : any
->a : ""
+>a : string
 >foo : any
 >1 : 1
 
diff --git a/tests/baselines/reference/multipleRoundInferenceAfterError.js b/tests/baselines/reference/multipleRoundInferenceAfterError.js
new file mode 100644
index 0000000000000..372d154229872
--- /dev/null
+++ b/tests/baselines/reference/multipleRoundInferenceAfterError.js
@@ -0,0 +1,8 @@
+//// [multipleRoundInferenceAfterError.ts]
+// Fixes #18715
+declare function inference<T>(target: T, name: keyof T): void;
+inference({ a: 1, b: 2, c: 3, d(n) { return n } }, "d");
+
+
+//// [multipleRoundInferenceAfterError.js]
+inference({ a: 1, b: 2, c: 3, d: function (n) { return n; } }, "d");
diff --git a/tests/baselines/reference/multipleRoundInferenceAfterError.symbols b/tests/baselines/reference/multipleRoundInferenceAfterError.symbols
new file mode 100644
index 0000000000000..05aae7f056991
--- /dev/null
+++ b/tests/baselines/reference/multipleRoundInferenceAfterError.symbols
@@ -0,0 +1,19 @@
+=== tests/cases/compiler/multipleRoundInferenceAfterError.ts ===
+// Fixes #18715
+declare function inference<T>(target: T, name: keyof T): void;
+>inference : Symbol(inference, Decl(multipleRoundInferenceAfterError.ts, 0, 0))
+>T : Symbol(T, Decl(multipleRoundInferenceAfterError.ts, 1, 27))
+>target : Symbol(target, Decl(multipleRoundInferenceAfterError.ts, 1, 30))
+>T : Symbol(T, Decl(multipleRoundInferenceAfterError.ts, 1, 27))
+>name : Symbol(name, Decl(multipleRoundInferenceAfterError.ts, 1, 40))
+>T : Symbol(T, Decl(multipleRoundInferenceAfterError.ts, 1, 27))
+
+inference({ a: 1, b: 2, c: 3, d(n) { return n } }, "d");
+>inference : Symbol(inference, Decl(multipleRoundInferenceAfterError.ts, 0, 0))
+>a : Symbol(a, Decl(multipleRoundInferenceAfterError.ts, 2, 11))
+>b : Symbol(b, Decl(multipleRoundInferenceAfterError.ts, 2, 17))
+>c : Symbol(c, Decl(multipleRoundInferenceAfterError.ts, 2, 23))
+>d : Symbol(d, Decl(multipleRoundInferenceAfterError.ts, 2, 29))
+>n : Symbol(n, Decl(multipleRoundInferenceAfterError.ts, 2, 32))
+>n : Symbol(n, Decl(multipleRoundInferenceAfterError.ts, 2, 32))
+
diff --git a/tests/baselines/reference/multipleRoundInferenceAfterError.types b/tests/baselines/reference/multipleRoundInferenceAfterError.types
new file mode 100644
index 0000000000000..9878df88f5ef6
--- /dev/null
+++ b/tests/baselines/reference/multipleRoundInferenceAfterError.types
@@ -0,0 +1,25 @@
+=== tests/cases/compiler/multipleRoundInferenceAfterError.ts ===
+// Fixes #18715
+declare function inference<T>(target: T, name: keyof T): void;
+>inference : <T>(target: T, name: keyof T) => void
+>T : T
+>target : T
+>T : T
+>name : keyof T
+>T : T
+
+inference({ a: 1, b: 2, c: 3, d(n) { return n } }, "d");
+>inference({ a: 1, b: 2, c: 3, d(n) { return n } }, "d") : void
+>inference : <T>(target: T, name: keyof T) => void
+>{ a: 1, b: 2, c: 3, d(n) { return n } } : { a: number; b: number; c: number; d(n: any): any; }
+>a : number
+>1 : 1
+>b : number
+>2 : 2
+>c : number
+>3 : 3
+>d : (n: any) => any
+>n : any
+>n : any
+>"d" : "d"
+
diff --git a/tests/baselines/reference/typeInferenceConflictingCandidates.errors.txt b/tests/baselines/reference/typeInferenceConflictingCandidates.errors.txt
index c98b39cb4fec6..752ed5235402c 100644
--- a/tests/baselines/reference/typeInferenceConflictingCandidates.errors.txt
+++ b/tests/baselines/reference/typeInferenceConflictingCandidates.errors.txt
@@ -1,4 +1,4 @@
-tests/cases/compiler/typeInferenceConflictingCandidates.ts(3,7): error TS2345: Argument of type '3' is not assignable to parameter of type '""'.
+tests/cases/compiler/typeInferenceConflictingCandidates.ts(3,7): error TS2345: Argument of type '3' is not assignable to parameter of type 'string'.
 
 
 ==== tests/cases/compiler/typeInferenceConflictingCandidates.ts (1 errors) ====
@@ -6,4 +6,4 @@ tests/cases/compiler/typeInferenceConflictingCandidates.ts(3,7): error TS2345: A
     
     g("", 3, a => a);
           ~
-!!! error TS2345: Argument of type '3' is not assignable to parameter of type '""'.
\ No newline at end of file
+!!! error TS2345: Argument of type '3' is not assignable to parameter of type 'string'.
\ No newline at end of file
diff --git a/tests/baselines/reference/typeInferenceConflictingCandidates.types b/tests/baselines/reference/typeInferenceConflictingCandidates.types
index c04a8045cd77b..3fb99cbbb1551 100644
--- a/tests/baselines/reference/typeInferenceConflictingCandidates.types
+++ b/tests/baselines/reference/typeInferenceConflictingCandidates.types
@@ -17,7 +17,7 @@ g("", 3, a => a);
 >g : <T>(a: T, b: T, c: (t: T) => T) => T
 >"" : ""
 >3 : 3
->a => a : (a: any) => any
->a : any
->a : any
+>a => a : (a: string) => string
+>a : string
+>a : string
 
diff --git a/tests/cases/compiler/multipleRoundInferenceAfterError.ts b/tests/cases/compiler/multipleRoundInferenceAfterError.ts
new file mode 100644
index 0000000000000..b2bff4af5ed1a
--- /dev/null
+++ b/tests/cases/compiler/multipleRoundInferenceAfterError.ts
@@ -0,0 +1,3 @@
+// Fixes #18715
+declare function inference<T>(target: T, name: keyof T): void;
+inference({ a: 1, b: 2, c: 3, d(n) { return n } }, "d");
diff --git a/tests/cases/fourslash/genericFunctionSignatureHelp3.ts b/tests/cases/fourslash/genericFunctionSignatureHelp3.ts
index 5d4275d6ef944..053b0e684d08b 100644
--- a/tests/cases/fourslash/genericFunctionSignatureHelp3.ts
+++ b/tests/cases/fourslash/genericFunctionSignatureHelp3.ts
@@ -8,32 +8,32 @@
 ////function foo6<T>(x: number, callback: (y6: T) => number) { }
 ////function foo7<T>(x: number, callback: (y7: T) => number) { }
 //// IDE shows the results on the right of each line, fourslash says different
-////foo1(/*1*/               // signature help shows y as T
+////foo1(/*1*/               // signature help shows y as {}
 ////foo2(1,/*2*/             // signature help shows y as {}
-////foo3(1, (/*3*/           // signature help shows y as T
+////foo3(1, (/*3*/           // signature help shows y as {}
 ////foo4<string>(1,/*4*/     // signature help shows y as string
-////foo5<string>(1, (/*5*/   // signature help shows y as T
+////foo5<string>(1, (/*5*/   // signature help shows y as string
 ////foo6(1, </*6*/           // signature help shows y as {}
-////foo7(1, <string>(/*7*/   // signature help shows y as T
+////foo7(1, <string>(/*7*/   // signature help shows y as {}
 
 goTo.marker('1');
-verify.currentSignatureHelpIs('foo1<T>(x: number, callback: (y1: T) => number): void');
+verify.currentSignatureHelpIs('foo1(x: number, callback: (y1: {}) => number): void');
 
-// goTo.marker('2');
-// verify.currentSignatureHelpIs('foo2(x: number, callback: (y2: {}) => number): void');
+goTo.marker('2');
+verify.currentSignatureHelpIs('foo2(x: number, callback: (y2: {}) => number): void');
 
 goTo.marker('3');
-verify.currentSignatureHelpIs('foo3<T>(x: number, callback: (y3: T) => number): void');
+verify.currentSignatureHelpIs('foo3(x: number, callback: (y3: {}) => number): void');
 
-// goTo.marker('4');
-// verify.currentSignatureHelpIs('foo4(x: number, callback: (y4: string) => number): void');
+goTo.marker('4');
+verify.currentSignatureHelpIs('foo4(x: number, callback: (y4: string) => number): void');
 
 goTo.marker('5');
 verify.currentSignatureHelpIs('foo5(x: number, callback: (y5: string) => number): void');
 
 goTo.marker('6');
-// verify.currentSignatureHelpIs('foo6(x: number, callback: (y6: {}) => number): void');
+verify.currentSignatureHelpIs('foo6(x: number, callback: (y6: {}) => number): void');
 edit.insert('string>(null,null);'); // need to make this line parse so we can get reasonable LS answers to later tests
 
 goTo.marker('7');
-verify.currentSignatureHelpIs('foo7<T>(x: number, callback: (y7: T) => number): void');
+verify.currentSignatureHelpIs('foo7(x: number, callback: (y7: {}) => number): void');
diff --git a/tests/cases/fourslash/genericFunctionSignatureHelp3MultiFile.ts b/tests/cases/fourslash/genericFunctionSignatureHelp3MultiFile.ts
index b82d5e10664bc..d1476660654a9 100644
--- a/tests/cases/fourslash/genericFunctionSignatureHelp3MultiFile.ts
+++ b/tests/cases/fourslash/genericFunctionSignatureHelp3MultiFile.ts
@@ -24,23 +24,23 @@
 ////foo7(1, <string>(/*7*/   // signature help shows y as T
 
 goTo.marker('1');
-verify.currentSignatureHelpIs('foo1<T>(x: number, callback: (y1: T) => number): void');
+verify.currentSignatureHelpIs('foo1(x: number, callback: (y1: {}) => number): void');
 
-// goTo.marker('2');
-// verify.currentSignatureHelpIs('foo2(x: number, callback: (y2: {}) => number): void');
+goTo.marker('2');
+verify.currentSignatureHelpIs('foo2(x: number, callback: (y2: {}) => number): void');
 
 goTo.marker('3');
-verify.currentSignatureHelpIs('foo3<T>(x: number, callback: (y3: T) => number): void');
+verify.currentSignatureHelpIs('foo3(x: number, callback: (y3: {}) => number): void');
 
-// goTo.marker('4');
-// verify.currentSignatureHelpIs('foo4(x: number, callback: (y4: string) => number): void');
+goTo.marker('4');
+verify.currentSignatureHelpIs('foo4(x: number, callback: (y4: string) => number): void');
 
 goTo.marker('5');
 verify.currentSignatureHelpIs('foo5(x: number, callback: (y5: string) => number): void');
 
 goTo.marker('6');
-// verify.currentSignatureHelpIs('foo6(x: number, callback: (y6: {}) => number): void');
+verify.currentSignatureHelpIs('foo6(x: number, callback: (y6: {}) => number): void');
 edit.insert('string>(null,null);'); // need to make this line parse so we can get reasonable LS answers to later tests
 
 goTo.marker('7');
-verify.currentSignatureHelpIs('foo7<T>(x: number, callback: (y7: T) => number): void');
+verify.currentSignatureHelpIs('foo7(x: number, callback: (y7: {}) => number): void');