diff --git a/src/AS/Ping.c b/src/AS/Ping.c
index 88ac7cb..3a8ffb7 100644
--- a/src/AS/Ping.c
+++ b/src/AS/Ping.c
@@ -10,15 +10,16 @@
 
 #include <Matrix.h>
 
-void
+bool
 ASPing(const ParseeConfig *conf)
 {
     HttpClientContext *ctx = NULL;
     HashMap *json = NULL;
     char *path;
+    bool ret;
     if (!conf)
     {
-        return;
+        return false;
     }
 
     path = StrConcat(3,
@@ -33,7 +34,9 @@ ASPing(const ParseeConfig *conf)
     Free(path);
     json = HashMapCreate();
     ASAuthenticateRequest(conf, ctx);
-    ParseeSetRequestJSON(ctx, json);
+    ret = ParseeSetRequestJSON(ctx, json) == HTTP_OK;
     HttpClientContextFree(ctx);
     JsonFree(json);
+
+    return ret;
 }
diff --git a/src/Main.c b/src/Main.c
index cebb055..a9b0a50 100644
--- a/src/Main.c
+++ b/src/Main.c
@@ -58,6 +58,34 @@ static const Argument arguments[] =
 #undef Argument
 };
 
+void 
+ParseeCheckMatrix(void *datp)
+{
+    static volatile uint64_t streak = 0;
+    ParseeData *data = datp;
+    if (!ASPing(data->config))
+    {
+        Log(LOG_ERR, "Cannot reach '%s' properly...", data->config->homeserver_host);
+        if (++streak >= 5)
+        {
+            Log(LOG_ERR, "This has been at least the fifth time in a row.");
+            Log(LOG_ERR, "Please check if your homeserver is active.");
+            Log(LOG_ERR, "%s shall now exit...", NAME);
+
+            pthread_mutex_lock(&data->halt_lock);
+            data->halted = true;
+            pthread_mutex_unlock(&data->halt_lock);
+
+            XMPPFinishCompStream(data->jabber);
+            pthread_join(xmpp_thr, NULL);
+            Log(LOG_INFO, "Stopping server...");
+            HttpServerStop(data->server);
+        }
+        return;
+    }
+    streak = 0;
+}
+
 int
 Main(Array *args, HashMap *env)
 {
@@ -259,6 +287,7 @@ Main(Array *args, HashMap *env)
     Log(LOG_NOTICE, "Starting up local cronjobs...");
     cron = CronCreate(10 SECONDS);
     CronEvery(cron, 5 MINUTES, ParseeCleanup, conf.handlerArgs);
+    CronEvery(cron, 10 SECONDS, ParseeCheckMatrix, conf.handlerArgs);
     ParseeCleanup(conf.handlerArgs);
 
     CronStart(cron);
diff --git a/src/Routes/Ping.c b/src/Routes/Ping.c
new file mode 100644
index 0000000..a508336
--- /dev/null
+++ b/src/Routes/Ping.c
@@ -0,0 +1,38 @@
+#include <Routes.h>
+
+#include <Cytoplasm/Log.h>
+
+#include <Matrix.h>
+#include <AS.h>
+
+RouteHead(RoutePing, arr, argp)
+{
+    ParseeHttpArg *args = argp;
+    HashMap *request = NULL;
+    HashMap *response = NULL;
+    Array *events;
+    size_t i;
+    
+    response = ASVerifyRequest(args);
+    if (response)
+    {
+        goto end;
+    }
+    if (HttpRequestMethodGet(args->ctx) != HTTP_POST)
+    {
+        HttpResponseStatus(args->ctx, HTTP_METHOD_NOT_ALLOWED);
+        response = MatrixCreateError(
+            "M_UNRECOGNIZED",
+            "Path /ping only accepts POST as a valid method."
+        );
+        goto end;
+    }
+
+    RequestJSON();
+
+    response = HashMapCreate();
+end:
+    (void) arr;
+    JsonFree(request);
+    return response;
+}
diff --git a/src/include/AS.h b/src/include/AS.h
index 8afef6f..562d172 100644
--- a/src/include/AS.h
+++ b/src/include/AS.h
@@ -29,7 +29,7 @@ extern void ASAuthenticateRequest(const ParseeConfig *, HttpClientContext *);
 extern bool ASRegisterUser(const ParseeConfig *, char *);
 
 /* Pings the homeserver to get attention. */
-extern void ASPing(const ParseeConfig *);
+extern bool ASPing(const ParseeConfig *);
 
 /** Joins a room from an {id} and a given {user} we want to masquerade 
  * as. 
diff --git a/src/include/Routes.h b/src/include/Routes.h
index 369a0d7..8d233e6 100644
--- a/src/include/Routes.h
+++ b/src/include/Routes.h
@@ -74,6 +74,7 @@ typedef struct ParseeCmdArg {
                     X_ROUTE("/_matrix/app/v1/transactions/(.*)", RouteTxns) \
                     X_ROUTE("/_matrix/app/v1/users/(.*)", RouteUserAck) \
                     X_ROUTE("/_matrix/app/v1/rooms/(.*)", RouteRoomAck) \
+                    X_ROUTE("/_matrix/app/v1/ping", RoutePing) \
                     X_ROUTE("/_matrix/client/v1/media/download/(.*)/(.*)", RouteMedia)
 
 #define X_ROUTE(path, name)     extern void * name(Array *, void *);