diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 869edfaffd4..1266af41840 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -2392,13 +2392,16 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
     }
 
     function isDeprecatedSymbol(symbol: Symbol) {
-        if (length(symbol.declarations) > 1) {
-            const parentSymbol = getParentOfSymbol(symbol);
-            if (parentSymbol && parentSymbol.flags & SymbolFlags.Interface) {
-                return some(symbol.declarations, d => !!(getCombinedNodeFlags(d) & NodeFlags.Deprecated));
-            }
+        const parentSymbol = getParentOfSymbol(symbol);
+        if (parentSymbol && length(symbol.declarations) > 1) {
+            return parentSymbol.flags & SymbolFlags.Interface ? some(symbol.declarations, isDeprecatedDeclaration) : every(symbol.declarations, isDeprecatedDeclaration);
         }
-        return !!(getDeclarationNodeFlagsFromSymbol(symbol) & NodeFlags.Deprecated);
+        return !!symbol.valueDeclaration && isDeprecatedDeclaration(symbol.valueDeclaration)
+            || length(symbol.declarations) && every(symbol.declarations, isDeprecatedDeclaration);
+    }
+
+    function isDeprecatedDeclaration(declaration: Declaration) {
+        return !!(getCombinedNodeFlags(declaration) & NodeFlags.Deprecated);
     }
 
     function addDeprecatedSuggestion(location: Node, declarations: Node[], deprecatedEntity: string) {
@@ -27886,7 +27889,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         }
 
         const localOrExportSymbol = getExportSymbolOfValueSymbolIfExported(symbol);
-        const targetSymbol = checkDeprecatedAliasedSymbol(localOrExportSymbol, node);
+        const targetSymbol = resolveAliasWithDeprecationCheck(localOrExportSymbol, node);
         if (isDeprecatedSymbol(targetSymbol) && isUncalledFunctionReference(node, targetSymbol) && targetSymbol.declarations) {
             addDeprecatedSuggestion(node, targetSymbol.declarations, node.escapedText as string);
         }
@@ -31550,8 +31553,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             }
         }
         else {
-            if (isDeprecatedSymbol(prop) && isUncalledFunctionReference(node, prop) && prop.declarations) {
-                addDeprecatedSuggestion(right, prop.declarations, right.escapedText as string);
+            const targetPropSymbol = resolveAliasWithDeprecationCheck(prop, right);
+            if (isDeprecatedSymbol(targetPropSymbol) && isUncalledFunctionReference(node, targetPropSymbol) && targetPropSymbol.declarations) {
+                addDeprecatedSuggestion(right, targetPropSymbol.declarations, right.escapedText as string);
             }
             checkPropertyNotUsedBeforeDeclaration(prop, node, right);
             markPropertyAsReferenced(prop, node, isSelfTypeAccess(left, parentSymbol));
@@ -44164,20 +44168,18 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             }
 
             if (isImportSpecifier(node)) {
-                const targetSymbol = checkDeprecatedAliasedSymbol(symbol, node);
-                if (isDeprecatedAliasedSymbol(targetSymbol) && targetSymbol.declarations) {
+                const targetSymbol = resolveAliasWithDeprecationCheck(symbol, node);
+                if (isDeprecatedSymbol(targetSymbol) && targetSymbol.declarations) {
                     addDeprecatedSuggestion(node, targetSymbol.declarations, targetSymbol.escapedName as string);
                 }
             }
         }
     }
 
-    function isDeprecatedAliasedSymbol(symbol: Symbol) {
-        return !!symbol.declarations && every(symbol.declarations, d => !!(getCombinedNodeFlags(d) & NodeFlags.Deprecated));
-    }
-
-    function checkDeprecatedAliasedSymbol(symbol: Symbol, location: Node) {
-        if (!(symbol.flags & SymbolFlags.Alias)) return symbol;
+    function resolveAliasWithDeprecationCheck(symbol: Symbol, location: Node) {
+        if (!(symbol.flags & SymbolFlags.Alias) || isDeprecatedSymbol(symbol) || !getDeclarationOfAliasSymbol(symbol)) {
+            return symbol;
+        }
 
         const targetSymbol = resolveAlias(symbol);
         if (targetSymbol === unknownSymbol) return targetSymbol;
@@ -44187,7 +44189,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             if (target) {
                 if (target === targetSymbol) break;
                 if (target.declarations && length(target.declarations)) {
-                    if (isDeprecatedAliasedSymbol(target)) {
+                    if (isDeprecatedSymbol(target)) {
                         addDeprecatedSuggestion(location, target.declarations, target.escapedName as string);
                         break;
                     }
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion20.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion20.ts
new file mode 100644
index 00000000000..46c190db289
--- /dev/null
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion20.ts
@@ -0,0 +1,37 @@
+///<reference path="fourslash.ts" />
+
+// @module: esnext
+// @filename: /a.ts
+////export default function a() {}
+
+// @filename: /b.ts
+////import _a from "./a";
+////export {
+////	/** @deprecated a is deprecated */
+////	_a as a,
+////};
+/////** @deprecated b is deprecated */
+////export const b = (): void => {};
+
+// @filename: /c.ts
+////import * as _ from "./b";
+////
+////_.[|a|]()
+////_.[|b|]()
+
+goTo.file("/c.ts")
+verify.getSuggestionDiagnostics([
+    {
+        "code": 6385,
+        "message": "'a' is deprecated.",
+        "reportsDeprecated": true,
+        "range": test.ranges()[0]
+    },
+    {
+        "code": 6385,
+        "message": "'b' is deprecated.",
+        "reportsDeprecated": true,
+        "range": test.ranges()[1]
+    },
+]);
+
diff --git a/tests/cases/fourslash/jsdocDeprecated_suggestion21.ts b/tests/cases/fourslash/jsdocDeprecated_suggestion21.ts
new file mode 100644
index 00000000000..4fdc2bc69f7
--- /dev/null
+++ b/tests/cases/fourslash/jsdocDeprecated_suggestion21.ts
@@ -0,0 +1,31 @@
+/// <reference path="fourslash.ts" />
+
+// @module: esnext
+// @filename: /a.ts
+////export const a = 1;
+////export const b = 1;
+
+// @filename: /b.ts
+////export {
+////    /** @deprecated a is deprecated */
+////    a
+////} from "./a";
+
+// @filename: /c.ts
+////export {
+////    a
+////} from "./b";
+
+// @filename: /d.ts
+////import * as _ from "./c";
+////_.[|a|]
+
+goTo.file("/d.ts")
+verify.getSuggestionDiagnostics([
+    {
+        "code": 6385,
+        "message": "'a' is deprecated.",
+        "reportsDeprecated": true,
+        "range": test.ranges()[0]
+    },
+]);