diff --git a/pyrdp/mitm/DeviceRedirectionMITM.py b/pyrdp/mitm/DeviceRedirectionMITM.py
index 881c4fbf7..20e5c778b 100644
--- a/pyrdp/mitm/DeviceRedirectionMITM.py
+++ b/pyrdp/mitm/DeviceRedirectionMITM.py
@@ -1,6 +1,6 @@
 #
 # This file is part of the PyRDP project.
-# Copyright (C) 2019-2020 GoSecure Inc.
+# Copyright (C) 2019-2021 GoSecure Inc.
 # Licensed under the GPLv3 or later.
 #
 
@@ -16,6 +16,7 @@
 from pyrdp.logging.StatCounter import StatCounter, STAT
 from pyrdp.mitm.FileMapping import FileMapping
 from pyrdp.mitm.state import RDPMITMState
+from pyrdp.mitm.TCPMITM import TCPMITM
 from pyrdp.pdu import DeviceAnnounce, DeviceCloseRequestPDU, DeviceCloseResponsePDU, DeviceCreateRequestPDU, \
     DeviceCreateResponsePDU, DeviceDirectoryControlResponsePDU, DeviceIORequestPDU, DeviceIOResponsePDU, \
     DeviceListAnnounceRequest, DeviceQueryDirectoryRequestPDU, DeviceQueryDirectoryResponsePDU, DeviceReadRequestPDU, \
@@ -52,13 +53,14 @@ class DeviceRedirectionMITM(Subject):
     FORGED_COMPLETION_ID = 1000000
 
     def __init__(self, client: DeviceRedirectionLayer, server: DeviceRedirectionLayer, log: LoggerAdapter,
-                 statCounter: StatCounter, state: RDPMITMState):
+                 statCounter: StatCounter, state: RDPMITMState, tcp: TCPMITM):
         """
         :param client: device redirection layer for the client side
         :param server: device redirection layer for the server side
         :param log: logger for this component
         :param statCounter: stat counter object
         :param state: shared RDP MITM state
+        :param tcp: TCP MITM component
         """
         super().__init__()
 
@@ -67,6 +69,7 @@ def __init__(self, client: DeviceRedirectionLayer, server: DeviceRedirectionLaye
         self.state = state
         self.log = log
         self.statCounter = statCounter
+        self.tcp = tcp
         self.mappings: Dict[(int, int), FileMapping] = {}
         self.filesystemRoot = self.config.filesystemDir / self.state.sessionID
 
@@ -90,6 +93,14 @@ def __init__(self, client: DeviceRedirectionLayer, server: DeviceRedirectionLaye
             onPDUReceived=self.onServerPDUReceived,
         )
 
+        self.tcp.client.createObserver(
+            onDisconnection=self.onDisconnection
+        )
+
+        self.tcp.server.createObserver(
+            onDisconnection=self.onDisconnection
+        )
+
     def deviceRoot(self, deviceID: int):
         return self.filesystemRoot / f"device{deviceID}"
 
@@ -102,6 +113,10 @@ def createDeviceRoot(self, deviceID: int):
     def config(self):
         return self.state.config
 
+    def onDisconnection(self, reason):
+        for mapping in self.mappings.values():
+            mapping.onDisconnection(reason)
+
     def onClientPDUReceived(self, pdu: DeviceRedirectionPDU):
         self.statCounter.increment(STAT.DEVICE_REDIRECTION, STAT.DEVICE_REDIRECTION_CLIENT)
         self.handlePDU(pdu, self.server)
diff --git a/pyrdp/mitm/FileMapping.py b/pyrdp/mitm/FileMapping.py
index 416918ec4..ac6fda09e 100644
--- a/pyrdp/mitm/FileMapping.py
+++ b/pyrdp/mitm/FileMapping.py
@@ -33,7 +33,8 @@ def __init__(self, file: io.BinaryIO, dataPath: Path, filesystemPath: Path, file
         self.written = False
 
     def seek(self, offset: int):
-        self.file.seek(offset)
+        if not self.file.closed:
+            self.file.seek(offset)
 
     def write(self, data: bytes):
         self.file.write(data)
@@ -54,6 +55,9 @@ def getSha1Hash(self):
         return sha1.hexdigest()
 
     def finalize(self):
+        if self.file.closed:
+            return
+
         self.log.debug("Closing file %(path)s", {"path": self.dataPath})
         self.file.close()
 
@@ -82,6 +86,11 @@ def finalize(self):
                 "path": str(self.filesystemPath.relative_to(self.filesystemDir)), "shasum": fileHash
             })
 
+    def onDisconnection(self, reason):
+        if not self.file.closed:
+            self.file.close()
+            Path(self.file.name).unlink(missing_ok=True)
+
     @staticmethod
     def generate(remotePath: str, outDir: Path, filesystemDir: Path, log: LoggerAdapter):
         remotePath = Path(remotePath.replace("\\", "/"))
diff --git a/pyrdp/mitm/RDPMITM.py b/pyrdp/mitm/RDPMITM.py
index 6e7058a96..9f5503f58 100644
--- a/pyrdp/mitm/RDPMITM.py
+++ b/pyrdp/mitm/RDPMITM.py
@@ -357,7 +357,7 @@ def buildDeviceChannel(self, client: MCSServerChannel, server: MCSClientChannel)
         LayerChainItem.chain(client, clientSecurity, clientVirtualChannel, clientLayer)
         LayerChainItem.chain(server, serverSecurity, serverVirtualChannel, serverLayer)
 
-        deviceRedirection = DeviceRedirectionMITM(clientLayer, serverLayer, self.getLog(MCSChannelName.DEVICE_REDIRECTION), self.statCounter, self.state)
+        deviceRedirection = DeviceRedirectionMITM(clientLayer, serverLayer, self.getLog(MCSChannelName.DEVICE_REDIRECTION), self.statCounter, self.state, self.tcp)
         self.channelMITMs[client.channelID] = deviceRedirection
 
         if self.config.enableCrawler:
diff --git a/test/test_DeviceRedirectionMITM.py b/test/test_DeviceRedirectionMITM.py
index cf5a1da74..5d0672f2e 100644
--- a/test/test_DeviceRedirectionMITM.py
+++ b/test/test_DeviceRedirectionMITM.py
@@ -29,7 +29,7 @@ def setUp(self):
         self.state = Mock()
         self.state.config = MagicMock()
         self.state.config.outDir = Path("/tmp")
-        self.mitm = DeviceRedirectionMITM(self.client, self.server, self.log, self.statCounter, self.state)
+        self.mitm = DeviceRedirectionMITM(self.client, self.server, self.log, self.statCounter, self.state, Mock())
 
     @patch("pyrdp.mitm.FileMapping.FileMapping.generate")
     def sendCreateResponse(self, request, response, generate):
diff --git a/test/test_FileMapping.py b/test/test_FileMapping.py
index 2c50b1c0d..58c00f77d 100644
--- a/test/test_FileMapping.py
+++ b/test/test_FileMapping.py
@@ -23,6 +23,7 @@ def createMapping(self, mkdir: MagicMock, mkstemp: MagicMock, mock_open_object):
         mkstemp.return_value = (1, str(self.outDir / "tmp" / "tmp_test"))
         mapping = FileMapping.generate("/test", self.outDir, Path("filesystems"), self.log)
         mapping.getSha1Hash = Mock(return_value = self.hash)
+        mapping.file.closed = False
         return mapping, mkdir, mkstemp, mock_open_object
 
     def test_generate_createsTempFile(self):
diff --git a/test/test_X224MITM.py b/test/test_X224MITM.py
index d6911c965..9e5813667 100644
--- a/test/test_X224MITM.py
+++ b/test/test_X224MITM.py
@@ -11,7 +11,7 @@
 from pyrdp.pdu import X224ConnectionRequestPDU, NegotiationRequestPDU
 
 
-class FileMappingTest(unittest.TestCase):
+class X224MITMTest(unittest.TestCase):
     def setUp(self):
         self.mitm = X224MITM(Mock(), Mock(), Mock(), Mock(), Mock(), MagicMock())