File transfer on macs is broken fairly consistently. It appears that it sometimes works for in-network transfers, but almost always fails for SOCKS5 or in-band. For test: Sender was Mac, receiver was Windows. No errors on Mac. Windows errors: SEVERE: There was an error during file transfer. Error in execution: – caused by: java.util.concurrent.ExecutionException: – caused by: No response from remote client: at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer.negotiateSt ream(IncomingFileTransfer.java:199) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer.access$100( IncomingFileTransfer.java:47) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer$1.run(Incom ingFileTransfer.java:124) at java.lang.Thread.run(Unknown Source) Nested Exception: java.util.concurrent.ExecutionException: – caused by: No response from remote client: at java.util.concurrent.FutureTask$Sync.innerGet(Unknown Source) at java.util.concurrent.FutureTask.get(Unknown Source) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer.negotiateSt ream(IncomingFileTransfer.java:193) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer.access$100( IncomingFileTransfer.java:47) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer$1.run(Incom ingFileTransfer.java:124) at java.lang.Thread.run(Unknown Source) Caused by: – caused by: No response from remote client: at org.jivesoftware.smackx.filetransfer.FaultTolerantNegotiator.createIn comingStream(FaultTolerantNegotiator.java:113) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer$2.call(Inco mingFileTransfer.java:186) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer$2.call(Inco mingFileTransfer.java:185) at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source) at java.util.concurrent.FutureTask.run(Unknown Source) at org.jivesoftware.smackx.filetransfer.IncomingFileTransfer.negotiateSt ream(IncomingFileTransfer.java:190) ... 3 more java.net.ConnectException: Connection timed out: connect at java.net.PlainSocketImpl.socketConnect(Native Method) at java.net.PlainSocketImpl.doConnect(Unknown Source) at java.net.PlainSocketImpl.connectToAddress(Unknown Source) at java.net.PlainSocketImpl.connect(Unknown Source) at java.net.SocksSocketImpl.connect(Unknown Source) at java.net.Socket.connect(Unknown Source) at java.net.Socket.connect(Unknown Source) at java.net.Socket.<init>(Unknown Source) at java.net.Socket.<init>(Unknown Source) at org.jivesoftware.smackx.filetransfer.Socks5TransferNegotiator.selectH ost(Socks5TransferNegotiator.java:196) at org.jivesoftware.smackx.filetransfer.Socks5TransferNegotiator.negotia teIncomingStream(Socks5TransferNegotiator.java:114) at org.jivesoftware.smackx.filetransfer.FaultTolerantNegotiator$Negotiat orService.call(FaultTolerantNegotiator.java:181) at org.jivesoftware.smackx.filetransfer.FaultTolerantNegotiator$Negotiat orService.call(FaultTolerantNegotiator.java:166) at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source) at java.util.concurrent.FutureTask.run(Unknown Source) at java.util.concurrent.Executors$RunnableAdapter.call(Unknown Source) at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source) at java.util.concurrent.FutureTask.run(Unknown Source) at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(Unknown Source ) at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source) at java.lang.Thread.run(Unknown Source) java.lang.InterruptedException at java.util.concurrent.locks.AbstractQueuedSynchronizer.acquireInterrup tibly(Unknown Source) at java.util.concurrent.locks.ReentrantLock.lockInterruptibly(Unknown So urce) at java.util.concurrent.ArrayBlockingQueue.put(Unknown Source) at org.jivesoftware.smack.PacketWriter.sendPacket(PacketWriter.java:106) at org.jivesoftware.smack.XMPPConnection.sendPacket(XMPPConnection.java: 670) at org.jivesoftware.smackx.filetransfer.Socks5TransferNegotiator.negotia teIncomingStream(Socks5TransferNegotiator.java:130) at org.jivesoftware.smackx.filetransfer.FaultTolerantNegotiator$Negotiat orService.call(FaultTolerantNegotiator.java:181) at org.jivesoftware.smackx.filetransfer.FaultTolerantNegotiator$Negotiat orService.call(FaultTolerantNegotiator.java:166) at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source) at java.util.concurrent.FutureTask.run(Unknown Source) at java.util.concurrent.Executors$RunnableAdapter.call(Unknown Source) at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source) at java.util.concurrent.FutureTask.run(Unknown Source) at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(Unknown Source ) at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source) at java.lang.Thread.run(Unknown Source)