diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 9ac19fb98d060..732f9ca04e019 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14505,7 +14505,8 @@ namespace ts {
                     inferFromTypes(getFalseTypeFromConditionalType(<ConditionalType>source), getFalseTypeFromConditionalType(<ConditionalType>target));
                 }
                 else if (target.flags & TypeFlags.Conditional) {
-                    inferFromTypes(source, getUnionType([getTrueTypeFromConditionalType(<ConditionalType>target), getFalseTypeFromConditionalType(<ConditionalType>target)]));
+                    inferFromTypes(source, getTrueTypeFromConditionalType(<ConditionalType>target));
+                    inferFromTypes(source, getFalseTypeFromConditionalType(<ConditionalType>target));
                 }
                 else if (target.flags & TypeFlags.UnionOrIntersection) {
                     for (const t of (<UnionOrIntersectionType>target).types) {
diff --git a/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.js b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.js
new file mode 100644
index 0000000000000..f066b18d5c64f
--- /dev/null
+++ b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.js
@@ -0,0 +1,39 @@
+//// [conditionalTypeRelaxingConstraintAssignability.ts]
+export type ElChildren =
+  | ElChildren.Void
+  | ElChildren.Text;
+export namespace ElChildren {
+  export type Void = undefined;
+  export type Text = string;
+}
+
+type Relax<C extends ElChildren> = C extends ElChildren.Text ? ElChildren.Text : C;
+
+export class Elem<
+  C extends ElChildren,
+  > {
+  constructor(
+    private children_: Relax<C>,
+  ) {
+  }
+}
+
+new Elem(undefined as ElChildren.Void);
+new Elem('' as ElChildren.Text);
+new Elem('' as ElChildren.Void | ElChildren.Text); // error
+new Elem('' as ElChildren); // error
+
+//// [conditionalTypeRelaxingConstraintAssignability.js]
+"use strict";
+exports.__esModule = true;
+var Elem = /** @class */ (function () {
+    function Elem(children_) {
+        this.children_ = children_;
+    }
+    return Elem;
+}());
+exports.Elem = Elem;
+new Elem(undefined);
+new Elem('');
+new Elem(''); // error
+new Elem(''); // error
diff --git a/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.symbols b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.symbols
new file mode 100644
index 0000000000000..7ce85b0fbfaf8
--- /dev/null
+++ b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.symbols
@@ -0,0 +1,73 @@
+=== tests/cases/compiler/conditionalTypeRelaxingConstraintAssignability.ts ===
+export type ElChildren =
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+
+  | ElChildren.Void
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Void : Symbol(ElChildren.Void, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 3, 29))
+
+  | ElChildren.Text;
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Text : Symbol(ElChildren.Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+
+export namespace ElChildren {
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+
+  export type Void = undefined;
+>Void : Symbol(Void, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 3, 29))
+
+  export type Text = string;
+>Text : Symbol(Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+}
+
+type Relax<C extends ElChildren> = C extends ElChildren.Text ? ElChildren.Text : C;
+>Relax : Symbol(Relax, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 6, 1))
+>C : Symbol(C, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 11))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>C : Symbol(C, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 11))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Text : Symbol(ElChildren.Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Text : Symbol(ElChildren.Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+>C : Symbol(C, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 11))
+
+export class Elem<
+>Elem : Symbol(Elem, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 83))
+
+  C extends ElChildren,
+>C : Symbol(C, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 10, 18))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+
+  > {
+  constructor(
+    private children_: Relax<C>,
+>children_ : Symbol(Elem.children_, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 13, 14))
+>Relax : Symbol(Relax, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 6, 1))
+>C : Symbol(C, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 10, 18))
+
+  ) {
+  }
+}
+
+new Elem(undefined as ElChildren.Void);
+>Elem : Symbol(Elem, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 83))
+>undefined : Symbol(undefined)
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Void : Symbol(ElChildren.Void, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 3, 29))
+
+new Elem('' as ElChildren.Text);
+>Elem : Symbol(Elem, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 83))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Text : Symbol(ElChildren.Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+
+new Elem('' as ElChildren.Void | ElChildren.Text); // error
+>Elem : Symbol(Elem, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 83))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Void : Symbol(ElChildren.Void, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 3, 29))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+>Text : Symbol(ElChildren.Text, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 4, 31))
+
+new Elem('' as ElChildren); // error
+>Elem : Symbol(Elem, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 8, 83))
+>ElChildren : Symbol(ElChildren, Decl(conditionalTypeRelaxingConstraintAssignability.ts, 0, 0), Decl(conditionalTypeRelaxingConstraintAssignability.ts, 2, 20))
+
diff --git a/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.types b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.types
new file mode 100644
index 0000000000000..c827e26bddb99
--- /dev/null
+++ b/tests/baselines/reference/conditionalTypeRelaxingConstraintAssignability.types
@@ -0,0 +1,64 @@
+=== tests/cases/compiler/conditionalTypeRelaxingConstraintAssignability.ts ===
+export type ElChildren =
+>ElChildren : ElChildren
+
+  | ElChildren.Void
+>ElChildren : any
+
+  | ElChildren.Text;
+>ElChildren : any
+
+export namespace ElChildren {
+  export type Void = undefined;
+>Void : undefined
+
+  export type Text = string;
+>Text : string
+}
+
+type Relax<C extends ElChildren> = C extends ElChildren.Text ? ElChildren.Text : C;
+>Relax : Relax<C>
+>ElChildren : any
+>ElChildren : any
+
+export class Elem<
+>Elem : Elem<C>
+
+  C extends ElChildren,
+  > {
+  constructor(
+    private children_: Relax<C>,
+>children_ : Relax<C>
+
+  ) {
+  }
+}
+
+new Elem(undefined as ElChildren.Void);
+>new Elem(undefined as ElChildren.Void) : Elem<undefined>
+>Elem : typeof Elem
+>undefined as ElChildren.Void : undefined
+>undefined : undefined
+>ElChildren : any
+
+new Elem('' as ElChildren.Text);
+>new Elem('' as ElChildren.Text) : Elem<string>
+>Elem : typeof Elem
+>'' as ElChildren.Text : string
+>'' : ""
+>ElChildren : any
+
+new Elem('' as ElChildren.Void | ElChildren.Text); // error
+>new Elem('' as ElChildren.Void | ElChildren.Text) : Elem<ElChildren>
+>Elem : typeof Elem
+>'' as ElChildren.Void | ElChildren.Text : ElChildren
+>'' : ""
+>ElChildren : any
+>ElChildren : any
+
+new Elem('' as ElChildren); // error
+>new Elem('' as ElChildren) : Elem<ElChildren>
+>Elem : typeof Elem
+>'' as ElChildren : ElChildren
+>'' : ""
+
diff --git a/tests/cases/compiler/conditionalTypeRelaxingConstraintAssignability.ts b/tests/cases/compiler/conditionalTypeRelaxingConstraintAssignability.ts
new file mode 100644
index 0000000000000..2f18e464e3b1d
--- /dev/null
+++ b/tests/cases/compiler/conditionalTypeRelaxingConstraintAssignability.ts
@@ -0,0 +1,24 @@
+// @strict: true
+export type ElChildren =
+  | ElChildren.Void
+  | ElChildren.Text;
+export namespace ElChildren {
+  export type Void = undefined;
+  export type Text = string;
+}
+
+type Relax<C extends ElChildren> = C extends ElChildren.Text ? ElChildren.Text : C;
+
+export class Elem<
+  C extends ElChildren,
+  > {
+  constructor(
+    private children_: Relax<C>,
+  ) {
+  }
+}
+
+new Elem(undefined as ElChildren.Void);
+new Elem('' as ElChildren.Text);
+new Elem('' as ElChildren.Void | ElChildren.Text); // error
+new Elem('' as ElChildren); // error
\ No newline at end of file