diff --git a/application/src/main/java/org/togetherjava/tjbot/features/utils/LinkDetection.java b/application/src/main/java/org/togetherjava/tjbot/features/utils/LinkDetection.java
index 3b6dc18112..d36f257b31 100644
--- a/application/src/main/java/org/togetherjava/tjbot/features/utils/LinkDetection.java
+++ b/application/src/main/java/org/togetherjava/tjbot/features/utils/LinkDetection.java
@@ -4,9 +4,14 @@
 import com.linkedin.urls.detection.UrlDetector;
 import com.linkedin.urls.detection.UrlDetectorOptions;
 
+import java.net.URI;
+import java.net.http.HttpClient;
+import java.net.http.HttpRequest;
+import java.net.http.HttpResponse;
 import java.util.List;
 import java.util.Optional;
 import java.util.Set;
+import java.util.concurrent.CompletableFuture;
 
 /**
  * Utility class to detect links.
@@ -58,6 +63,43 @@ public static boolean containsLink(String content) {
         return !(new UrlDetector(content, UrlDetectorOptions.BRACKET_MATCH).detect().isEmpty());
     }
 
+    public static CompletableFuture<Boolean> isLinkBroken(String url) {
+        HttpClient client = HttpClient.newHttpClient();
+
+        HttpRequest request = HttpRequest.newBuilder(URI.create(url))
+            .method("HEAD", HttpRequest.BodyPublishers.noBody())
+            .build();
+
+        return client.sendAsync(request, HttpResponse.BodyHandlers.discarding())
+            .thenApply(response -> response.statusCode() >= 400)
+            .exceptionally(ignored -> true);
+    }
+
+    public static CompletableFuture<String> replaceDeadLinks(String text, String replacement) {
+        Set<LinkFilter> filters = Set.of(LinkFilter.SUPPRESSED, LinkFilter.NON_HTTP_SCHEME);
+
+        List<String> links = extractLinks(text, filters);
+
+        if (links.isEmpty()) {
+            return CompletableFuture.completedFuture(text);
+        }
+
+        StringBuilder result = new StringBuilder(text);
+
+        List<CompletableFuture<Void>> checks =
+                links.stream().map(link -> isLinkBroken(link).thenAccept(isDead -> {
+                    if (isDead) {
+                        int index = result.indexOf(link);
+                        if (index != -1) {
+                            result.replace(index, index + link.length(), replacement);
+                        }
+                    }
+                })).toList();
+
+        return CompletableFuture.allOf(checks.toArray(new CompletableFuture[0]))
+            .thenApply(v -> result.toString());
+    }
+
     private static Optional<String> toLink(Url url, Set<LinkFilter> filter) {
         String raw = url.getOriginalUrl();
         if (filter.contains(LinkFilter.SUPPRESSED) && raw.contains(">")) {
@@ -76,7 +118,6 @@ private static Optional<String> toLink(Url url, Set<LinkFilter> filter) {
             // Remove trailing punctuation
             link = link.substring(0, link.length() - 1);
         }
-
         return Optional.of(link);
     }