diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 88c71bbfdf088..051f0c753b49d 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -32758,6 +32758,18 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 member = prop;
                 allPropertiesTable?.set(prop.escapedName, prop);
 
+                if (contextualType) {
+                    forEach(getPropertyOfType(contextualType, member.escapedName)?.declarations, declaration => {
+                        const symbol = getSymbolOfDeclaration(declaration);
+                        if (
+                            isDeprecatedSymbol(symbol) && symbol.declarations &&
+                            isTypeAssignableTo(type, getTypeOfSymbol(symbol))
+                        ) {
+                            addDeprecatedSuggestion(memberDecl.name, symbol.declarations, member.escapedName as string);
+                        }
+                    });
+                }
+
                 if (
                     contextualType && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) &&
                     (memberDecl.kind === SyntaxKind.PropertyAssignment || memberDecl.kind === SyntaxKind.MethodDeclaration) && isContextSensitive(memberDecl)
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion19.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion19.ts
index f70ae4b9b923f..6685eb5b64662 100644
--- a/tests/cases/fourslash/jsdocDeprecated_suggestion19.ts
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion19.ts
@@ -8,15 +8,20 @@
 ////    /** @deprecated  */
 ////    x: number;
 ////}
-////const foo: I = { x: 1, y: 1 };
+////const foo: I = { [|x|]: 1, y: 1 };
 ////foo.[|x|];
 
-const [range] = test.ranges();
 verify.getSuggestionDiagnostics([
     {
         "code": 6385,
         "message": "'x' is deprecated.",
         "reportsDeprecated": true,
-        "range": range
+        "range": test.ranges()[0]
+    },
+    {
+        "code": 6385,
+        "message": "'x' is deprecated.",
+        "reportsDeprecated": true,
+        "range": test.ranges()[1]
     },
 ]);
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion23.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion23.ts
new file mode 100644
index 0000000000000..99ec16f188edd
--- /dev/null
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion23.ts
@@ -0,0 +1,29 @@
+/// <reference path="fourslash.ts" />
+
+// @filename: /a.ts
+////type I = {
+////    /**
+////     * @deprecated
+////     */
+////    text: string;
+////} | {
+////    text: { a: string; b: string };
+////};
+////
+////const a: I = { [|text|]: "" };
+////a.[|text|];
+
+verify.getSuggestionDiagnostics([
+    {
+        code: 6385,
+        message: "'text' is deprecated.",
+        reportsDeprecated: true,
+        range: test.ranges()[0]
+    },
+    {
+        code: 6385,
+        message: "'text' is deprecated.",
+        reportsDeprecated: true,
+        range: test.ranges()[1]
+    },
+]);
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion24.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion24.ts
new file mode 100644
index 0000000000000..681a45a4f2910
--- /dev/null
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion24.ts
@@ -0,0 +1,21 @@
+/// <reference path="fourslash.ts" />
+
+// @filename: /a.ts
+////type I = {
+////    /**
+////     * @deprecated
+////     */
+////    text: string;
+////};
+////
+////function f(i: I) { return i; }
+////f({ [|text|]: 'a' });
+
+verify.getSuggestionDiagnostics([
+    {
+        code: 6385,
+        message: "'text' is deprecated.",
+        reportsDeprecated: true,
+        range: test.ranges()[0]
+    },
+]);
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion25.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion25.ts
new file mode 100644
index 0000000000000..d6eb02e239faa
--- /dev/null
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion25.ts
@@ -0,0 +1,21 @@
+/// <reference path="fourslash.ts" />
+
+// @filename: /a.ts
+////interface A {
+////    a: number;
+////}
+////interface B {
+////    /** @deprecated */
+////    a: string;
+////}
+////const a: A | B  = { [|a|]: 'a' }
+////const b: A | B  = { [|a|]: 1 }
+
+verify.getSuggestionDiagnostics([
+    {
+        code: 6385,
+        message: "'a' is deprecated.",
+        reportsDeprecated: true,
+        range: test.ranges()[0],
+    },
+]);