Index: src/OFEpollKernelEventObserver.m
==================================================================
--- src/OFEpollKernelEventObserver.m
+++ src/OFEpollKernelEventObserver.m
@@ -128,13 +128,19 @@
 	    objectForKey: (void *)((intptr_t)fd + 1)];
 	events &= ~removeEvents;
 
 	if (events == 0) {
 		if (epoll_ctl(_epfd, EPOLL_CTL_DEL, fd, NULL) == -1)
-			@throw [OFObserveFailedException
-			    exceptionWithObserver: self
-					    errNo: errno];
+			/*
+			 * When an async connect fails, it seems the socket is
+			 * automatically removed from epoll, meaning ENOENT is
+			 * returned when we try to remove it after it failed.
+			 */
+			if (errno != ENOENT)
+				@throw [OFObserveFailedException
+				    exceptionWithObserver: self
+						    errNo: errno];
 
 		[_FDToEvents removeObjectForKey: (void *)((intptr_t)fd + 1)];
 	} else {
 		struct epoll_event event;
 

Index: src/OFRunLoop.m
==================================================================
--- src/OFRunLoop.m
+++ src/OFRunLoop.m
@@ -702,13 +702,32 @@
 				 port: 0
 			       socket: object
 				errNo: errNo];
 
 	if ([_delegate respondsToSelector:
-	    @selector(of_socketDidConnect:exception:)])
-		[_delegate of_socketDidConnect: object
-				     exception: exception];
+	    @selector(of_socketDidConnect:exception:)]) {
+		/*
+		 * Make sure we only call the delegate once we removed the
+		 * socket from the kernel event observer. This is necessary as
+		 * otherwise we could try to connect to the next address and it
+		 * would not be re-registered with the kernel event observer,
+		 * which is necessary for some kernel event observers (e.g.
+		 * epoll) even if the fd of the new socket is the same.
+		 */
+		OFRunLoop *runLoop = [OFRunLoop currentRunLoop];
+		OFTimer *timer = [OFTimer
+		    timerWithTimeInterval: 0
+				   target: _delegate
+				 selector: @selector(of_socketDidConnect:
+					       exception:)
+				   object: object
+				   object: exception
+				  repeats: false];
+
+		[runLoop addTimer: timer
+			  forMode: runLoop.currentMode];
+	}
 
 	return false;
 }
 @end
 # endif