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..f98cb6c06d 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
@@ -4,27 +4,62 @@
 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.
+ * Utility methods for working with links inside arbitrary text.
+ *
+ * <p>
+ * This class can:
+ * <ul>
+ * <li>Extract HTTP(S) links from text</li>
+ * <li>Check whether a link is reachable via HTTP</li>
+ * <li>Replace broken links asynchronously</li>
+ * </ul>
+ *
+ * <p>
+ * It is intentionally stateless and uses asynchronous HTTP requests to avoid blocking calling
+ * threads.
  */
+
 public class LinkDetection {
+    private static final HttpClient HTTP_CLIENT = HttpClient.newHttpClient();
 
     /**
-     * Possible ways to filter a link.
+     * Default filters applied when extracting links from text.
      *
-     * @see LinkDetection
+     * <p>
+     * Links to intentionally ignore in order to reduce false positives when scanning chat messages
+     * or source-code snippets.
+     */
+
+    private static final Set<LinkFilter> DEFAULT_FILTERS =
+            Set.of(LinkFilter.SUPPRESSED, LinkFilter.NON_HTTP_SCHEME);
+
+    /**
+     * Filters that control which detected URLs are returned by {@link #extractLinks}.
      */
     public enum LinkFilter {
         /**
-         * Filters links suppressed with {@literal <url>}.
+         * Ignores URLs that are wrapped in angle brackets, e.g. {@code <https://example.com>}.
+         *
+         * <p>
+         * Such links are often intentionally suppressed in chat platforms.
          */
         SUPPRESSED,
         /**
-         * Filters links that are not using http scheme.
+         * Ignores URLs that do not use the HTTP or HTTPS scheme.
+         *
+         * <p>
+         * This helps avoid false positives such as {@code ftp://}, {@code file://}, or scheme-less
+         * matches.
          */
         NON_HTTP_SCHEME
     }
@@ -34,30 +69,187 @@ private LinkDetection() {
     }
 
     /**
-     * Extracts all links from the given content.
+     * Extracts links from the given text.
+     *
+     * <p>
+     * The text is scanned using a URL detector, then filtered and normalized according to the
+     * provided {@link LinkFilter}s.
+     *
+     * <p>
+     * Example:
      *
-     * @param content the content to search through
-     * @param filter the filters applied to the urls
-     * @return a list of all found links, can be empty
+     * <pre>{@code
+     * Set<LinkFilter> filters = Set.of(LinkFilter.SUPPRESSED, LinkFilter.NON_HTTP_SCHEME);
+     * extractLinks("Visit https://example.com and <ftp://skip.me>", filters)
+     * // returns ["https://example.com"]
+     * }</pre>
+     *
+     * @param content the text to scan for links
+     * @param filter a set of filters controlling which detected links are returned
+     * @return a list of extracted links in the order they appear in the text
      */
+
     public static List<String> extractLinks(String content, Set<LinkFilter> filter) {
         return new UrlDetector(content, UrlDetectorOptions.BRACKET_MATCH).detect()
-            .stream()
-            .map(url -> toLink(url, filter))
-            .flatMap(Optional::stream)
-            .toList();
+                .stream()
+                .map(url -> toLink(url, filter))
+                .flatMap(Optional::stream)
+                .toList();
     }
 
     /**
-     * Checks whether the given content contains a link.
+     * Extracts links from the given text using default filters.
+     *
+     * <p>
+     * This is a convenience method that uses {@link #DEFAULT_FILTERS}.
      *
-     * @param content the content to search through
-     * @return true if the content contains at least one link
+     * @param content the text to scan for links
+     * @return a list of extracted links in the order they appear in the text
+     * @see #extractLinks(String, Set)
      */
+    public static List<String> extractLinks(String content) {
+        return extractLinks(content, DEFAULT_FILTERS);
+    }
+
+    /**
+     * Checks whether the given text contains at least one detectable URL.
+     *
+     * <p>
+     * This method performs a lightweight detection only and does not apply any {@link LinkFilter}s.
+     *
+     * @param content the text to scan
+     * @return {@code true} if at least one URL-like pattern is detected
+     */
+
     public static boolean containsLink(String content) {
         return !(new UrlDetector(content, UrlDetectorOptions.BRACKET_MATCH).detect().isEmpty());
     }
 
+    /**
+     * Asynchronously checks whether a URL is considered broken.
+     *
+     * <p>
+     * A link is considered broken if:
+     * <ul>
+     * <li>The URL is malformed or unreachable</li>
+     * <li>The HTTP request fails with an exception</li>
+     * <li>The response status code is 4xx (client error) or 5xx (server error)</li>
+     * </ul>
+     *
+     * <p>
+     * Successful responses (2xx) and redirects (3xx) are considered valid links. The response body
+     * is never inspected.
+     *
+     * @param url the URL to check
+     * @return a {@code CompletableFuture} completing with {@code true} if the link is broken,
+     *         {@code false} otherwise
+     */
+
+    public static CompletableFuture<Boolean> isLinkBroken(String url) {
+        // Try HEAD request first (cheap and fast)
+        HttpRequest headRequest = HttpRequest.newBuilder(URI.create(url))
+                .method("HEAD", HttpRequest.BodyPublishers.noBody())
+                .build();
+
+        return HTTP_CLIENT.sendAsync(headRequest, HttpResponse.BodyHandlers.discarding())
+                .thenApply(response -> {
+                    int status = response.statusCode();
+                    // 2xx and 3xx are success, 4xx and 5xx are errors
+                    return status >= 400;
+                })
+                .exceptionally(_ -> true)
+                .thenCompose(result -> {
+                    if (!Boolean.TRUE.equals(result)) {
+                        return CompletableFuture.completedFuture(false);
+                    }
+                    // If HEAD fails, fall back to GET request (some servers don't support HEAD)
+                    HttpRequest fallbackGetRequest =
+                            HttpRequest.newBuilder(URI.create(url)).GET().build();
+                    return HTTP_CLIENT
+                            .sendAsync(fallbackGetRequest, HttpResponse.BodyHandlers.discarding())
+                            .thenApply(resp -> resp.statusCode() >= 400)
+                            .exceptionally(_ -> true);
+                });
+    }
+
+    /**
+     * Replaces all broken links in the given text.
+     *
+     * <p>
+     * Each detected link is checked asynchronously using {@link #isLinkBroken(String)}. Only links
+     * confirmed as broken are replaced. Duplicate URLs are checked only once and all occurrences
+     * are replaced if found to be broken.
+     *
+     * <p>
+     * This method does not block - all link checks are performed asynchronously and combined into a
+     * single {@code CompletableFuture}.
+     *
+     * <p>
+     * Example:
+     *
+     * <pre>{@code
+     * replaceBrokenLinks("""
+     *           Test
+     *           http://deadlink/1
+     *           http://workinglink/1
+     *         """, "(broken link)")
+     * }</pre>
+     *
+     * <p>
+     * Results in:
+     *
+     * <pre>{@code
+     * Test
+     * (broken link)
+     * http://workinglink/1
+     * }</pre>
+     *
+     * @param text the input text containing URLs
+     * @param replacement the string used to replace broken links
+     * @return a {@code CompletableFuture} that completes with the modified text, or the original
+     *         text if no broken links were found
+     */
+
+    public static CompletableFuture<String> replaceBrokenLinks(String text, String replacement) {
+        List<String> links = extractLinks(text, DEFAULT_FILTERS);
+
+        if (links.isEmpty()) {
+            return CompletableFuture.completedFuture(text);
+        }
+
+        List<CompletableFuture<Optional<String>>> brokenLinkFutures = links.stream()
+                .distinct()
+                .map(link -> isLinkBroken(link)
+                        .thenApply(isBroken -> Boolean.TRUE.equals(isBroken) ? Optional.of(link) : Optional.<String>empty()))
+                .toList();
+
+        return CompletableFuture.allOf(brokenLinkFutures.toArray(new CompletableFuture[0]))
+                .thenApply(_ -> brokenLinkFutures.stream()
+                        .map(CompletableFuture::join)
+                        .flatMap(Optional::stream)
+                        .toList())
+                .thenApply(brokenLinks -> {
+                    String result = text;
+                    for (String brokenLink : brokenLinks) {
+                        result = result.replace(brokenLink, replacement);
+                    }
+                    return result;
+                });
+    }
+
+    /**
+     * Converts a detected {@link Url} into a normalized link string.
+     *
+     * <p>
+     * Applies the provided {@link LinkFilter}s. Additionally removes trailing punctuation such as
+     * commas or periods from the detected URL.
+     *
+     * @param url the detected URL
+     * @param filter active link filters to apply
+     * @return an {@link Optional} containing the normalized link, or {@code Optional.empty()} if
+     *         the link should be filtered out
+     */
+
     private static Optional<String> toLink(Url url, Set<LinkFilter> filter) {
         String raw = url.getOriginalUrl();
         if (filter.contains(LinkFilter.SUPPRESSED) && raw.contains(">")) {
@@ -76,8 +268,6 @@ private static Optional<String> toLink(Url url, Set<LinkFilter> filter) {
             // Remove trailing punctuation
             link = link.substring(0, link.length() - 1);
         }
-
         return Optional.of(link);
     }
-
-}
+}
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