diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 1edbb1d4a0dd3..778d5e2dfa736 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -22691,7 +22691,7 @@ namespace ts {
             const keyPropertyName = getKeyPropertyName(unionType);
             const propNode = keyPropertyName && find(node.properties, p => p.symbol && p.kind === SyntaxKind.PropertyAssignment &&
                 p.symbol.escapedName === keyPropertyName && isPossiblyDiscriminantValue(p.initializer));
-            const propType = propNode && getTypeOfExpression((propNode as PropertyAssignment).initializer);
+            const propType = propNode && getContextFreeTypeOfExpression((propNode as PropertyAssignment).initializer);
             return propType && getConstituentTypeForKeyType(unionType, propType);
         }
 
@@ -26198,7 +26198,7 @@ namespace ts {
                 concatenate(
                     map(
                         filter(node.properties, p => !!p.symbol && p.kind === SyntaxKind.JsxAttribute && isDiscriminantProperty(contextualType, p.symbol.escapedName) && (!p.initializer || isPossiblyDiscriminantValue(p.initializer))),
-                        prop => ([!(prop as JsxAttribute).initializer ? (() => trueType) : (() => checkExpression((prop as JsxAttribute).initializer!)), prop.symbol.escapedName] as [() => Type, __String])
+                        prop => ([!(prop as JsxAttribute).initializer ? (() => trueType) : (() => getContextFreeTypeOfExpression((prop as JsxAttribute).initializer!)), prop.symbol.escapedName] as [() => Type, __String])
                     ),
                     map(
                         filter(getPropertiesOfType(contextualType), s => !!(s.flags & SymbolFlags.Optional) && !!node?.symbol?.members && !node.symbol.members.has(s.escapedName) && isDiscriminantProperty(contextualType, s.escapedName)),
diff --git a/tests/baselines/reference/discriminatedUnionJsxElement.js b/tests/baselines/reference/discriminatedUnionJsxElement.js
new file mode 100644
index 0000000000000..ca5b766aac92f
--- /dev/null
+++ b/tests/baselines/reference/discriminatedUnionJsxElement.js
@@ -0,0 +1,57 @@
+//// [discriminatedUnionJsxElement.tsx]
+// Repro from #46021
+
+interface IData<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine> {
+    menuItemsVariant?: MenuItemVariant;
+}
+
+function Menu<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>) {
+    const listItemVariant = data.menuItemsVariant ?? ListItemVariant.OneLine;
+    return <ListItem variant={listItemVariant} />;
+}
+
+type IListItemData = { variant: ListItemVariant.Avatar; } | { variant: ListItemVariant.OneLine; };
+
+enum ListItemVariant {
+    OneLine,
+    Avatar,
+}
+
+function ListItem(_data: IListItemData) {
+    return null; 
+}
+
+
+//// [discriminatedUnionJsxElement.jsx]
+"use strict";
+// Repro from #46021
+function Menu(data) {
+    var _a;
+    var listItemVariant = (_a = data.menuItemsVariant) !== null && _a !== void 0 ? _a : ListItemVariant.OneLine;
+    return <ListItem variant={listItemVariant}/>;
+}
+var ListItemVariant;
+(function (ListItemVariant) {
+    ListItemVariant[ListItemVariant["OneLine"] = 0] = "OneLine";
+    ListItemVariant[ListItemVariant["Avatar"] = 1] = "Avatar";
+})(ListItemVariant || (ListItemVariant = {}));
+function ListItem(_data) {
+    return null;
+}
+
+
+//// [discriminatedUnionJsxElement.d.ts]
+interface IData<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine> {
+    menuItemsVariant?: MenuItemVariant;
+}
+declare function Menu<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>): any;
+declare type IListItemData = {
+    variant: ListItemVariant.Avatar;
+} | {
+    variant: ListItemVariant.OneLine;
+};
+declare enum ListItemVariant {
+    OneLine = 0,
+    Avatar = 1
+}
+declare function ListItem(_data: IListItemData): null;
diff --git a/tests/baselines/reference/discriminatedUnionJsxElement.symbols b/tests/baselines/reference/discriminatedUnionJsxElement.symbols
new file mode 100644
index 0000000000000..aa884f5a1b0a8
--- /dev/null
+++ b/tests/baselines/reference/discriminatedUnionJsxElement.symbols
@@ -0,0 +1,67 @@
+=== tests/cases/compiler/discriminatedUnionJsxElement.tsx ===
+// Repro from #46021
+
+interface IData<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine> {
+>IData : Symbol(IData, Decl(discriminatedUnionJsxElement.tsx, 0, 0))
+>MenuItemVariant : Symbol(MenuItemVariant, Decl(discriminatedUnionJsxElement.tsx, 2, 16))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+
+    menuItemsVariant?: MenuItemVariant;
+>menuItemsVariant : Symbol(IData.menuItemsVariant, Decl(discriminatedUnionJsxElement.tsx, 2, 84))
+>MenuItemVariant : Symbol(MenuItemVariant, Decl(discriminatedUnionJsxElement.tsx, 2, 16))
+}
+
+function Menu<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>) {
+>Menu : Symbol(Menu, Decl(discriminatedUnionJsxElement.tsx, 4, 1))
+>MenuItemVariant : Symbol(MenuItemVariant, Decl(discriminatedUnionJsxElement.tsx, 6, 14))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+>data : Symbol(data, Decl(discriminatedUnionJsxElement.tsx, 6, 81))
+>IData : Symbol(IData, Decl(discriminatedUnionJsxElement.tsx, 0, 0))
+>MenuItemVariant : Symbol(MenuItemVariant, Decl(discriminatedUnionJsxElement.tsx, 6, 14))
+
+    const listItemVariant = data.menuItemsVariant ?? ListItemVariant.OneLine;
+>listItemVariant : Symbol(listItemVariant, Decl(discriminatedUnionJsxElement.tsx, 7, 9))
+>data.menuItemsVariant : Symbol(IData.menuItemsVariant, Decl(discriminatedUnionJsxElement.tsx, 2, 84))
+>data : Symbol(data, Decl(discriminatedUnionJsxElement.tsx, 6, 81))
+>menuItemsVariant : Symbol(IData.menuItemsVariant, Decl(discriminatedUnionJsxElement.tsx, 2, 84))
+>ListItemVariant.OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+
+    return <ListItem variant={listItemVariant} />;
+>ListItem : Symbol(ListItem, Decl(discriminatedUnionJsxElement.tsx, 16, 1))
+>variant : Symbol(variant, Decl(discriminatedUnionJsxElement.tsx, 8, 20))
+>listItemVariant : Symbol(listItemVariant, Decl(discriminatedUnionJsxElement.tsx, 7, 9))
+}
+
+type IListItemData = { variant: ListItemVariant.Avatar; } | { variant: ListItemVariant.OneLine; };
+>IListItemData : Symbol(IListItemData, Decl(discriminatedUnionJsxElement.tsx, 9, 1))
+>variant : Symbol(variant, Decl(discriminatedUnionJsxElement.tsx, 11, 22))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>Avatar : Symbol(ListItemVariant.Avatar, Decl(discriminatedUnionJsxElement.tsx, 14, 12))
+>variant : Symbol(variant, Decl(discriminatedUnionJsxElement.tsx, 11, 61))
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+>OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+
+enum ListItemVariant {
+>ListItemVariant : Symbol(ListItemVariant, Decl(discriminatedUnionJsxElement.tsx, 11, 98))
+
+    OneLine,
+>OneLine : Symbol(ListItemVariant.OneLine, Decl(discriminatedUnionJsxElement.tsx, 13, 22))
+
+    Avatar,
+>Avatar : Symbol(ListItemVariant.Avatar, Decl(discriminatedUnionJsxElement.tsx, 14, 12))
+}
+
+function ListItem(_data: IListItemData) {
+>ListItem : Symbol(ListItem, Decl(discriminatedUnionJsxElement.tsx, 16, 1))
+>_data : Symbol(_data, Decl(discriminatedUnionJsxElement.tsx, 18, 18))
+>IListItemData : Symbol(IListItemData, Decl(discriminatedUnionJsxElement.tsx, 9, 1))
+
+    return null; 
+}
+
diff --git a/tests/baselines/reference/discriminatedUnionJsxElement.types b/tests/baselines/reference/discriminatedUnionJsxElement.types
new file mode 100644
index 0000000000000..54ca2b4268f54
--- /dev/null
+++ b/tests/baselines/reference/discriminatedUnionJsxElement.types
@@ -0,0 +1,57 @@
+=== tests/cases/compiler/discriminatedUnionJsxElement.tsx ===
+// Repro from #46021
+
+interface IData<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine> {
+>ListItemVariant : any
+
+    menuItemsVariant?: MenuItemVariant;
+>menuItemsVariant : MenuItemVariant | undefined
+}
+
+function Menu<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>) {
+>Menu : <MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>) => any
+>ListItemVariant : any
+>data : IData<MenuItemVariant>
+
+    const listItemVariant = data.menuItemsVariant ?? ListItemVariant.OneLine;
+>listItemVariant : ListItemVariant.OneLine | NonNullable<MenuItemVariant>
+>data.menuItemsVariant ?? ListItemVariant.OneLine : ListItemVariant.OneLine | NonNullable<MenuItemVariant>
+>data.menuItemsVariant : MenuItemVariant | undefined
+>data : IData<MenuItemVariant>
+>menuItemsVariant : MenuItemVariant | undefined
+>ListItemVariant.OneLine : ListItemVariant.OneLine
+>ListItemVariant : typeof ListItemVariant
+>OneLine : ListItemVariant.OneLine
+
+    return <ListItem variant={listItemVariant} />;
+><ListItem variant={listItemVariant} /> : error
+>ListItem : (_data: IListItemData) => null
+>variant : ListItemVariant
+>listItemVariant : ListItemVariant
+}
+
+type IListItemData = { variant: ListItemVariant.Avatar; } | { variant: ListItemVariant.OneLine; };
+>IListItemData : IListItemData
+>variant : ListItemVariant.Avatar
+>ListItemVariant : any
+>variant : ListItemVariant.OneLine
+>ListItemVariant : any
+
+enum ListItemVariant {
+>ListItemVariant : ListItemVariant
+
+    OneLine,
+>OneLine : ListItemVariant.OneLine
+
+    Avatar,
+>Avatar : ListItemVariant.Avatar
+}
+
+function ListItem(_data: IListItemData) {
+>ListItem : (_data: IListItemData) => null
+>_data : IListItemData
+
+    return null; 
+>null : null
+}
+
diff --git a/tests/cases/compiler/discriminatedUnionJsxElement.tsx b/tests/cases/compiler/discriminatedUnionJsxElement.tsx
new file mode 100644
index 0000000000000..b000c2fb2a032
--- /dev/null
+++ b/tests/cases/compiler/discriminatedUnionJsxElement.tsx
@@ -0,0 +1,25 @@
+// @strict: true
+// @declaration: true
+// @jsx: preserve
+
+// Repro from #46021
+
+interface IData<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine> {
+    menuItemsVariant?: MenuItemVariant;
+}
+
+function Menu<MenuItemVariant extends ListItemVariant = ListItemVariant.OneLine>(data: IData<MenuItemVariant>) {
+    const listItemVariant = data.menuItemsVariant ?? ListItemVariant.OneLine;
+    return <ListItem variant={listItemVariant} />;
+}
+
+type IListItemData = { variant: ListItemVariant.Avatar; } | { variant: ListItemVariant.OneLine; };
+
+enum ListItemVariant {
+    OneLine,
+    Avatar,
+}
+
+function ListItem(_data: IListItemData) {
+    return null; 
+}