diff --git a/t/test.py b/t/test.py
index 6c45391..6fa8b52 100644
--- a/t/test.py
+++ b/t/test.py
@@ -437,9 +437,8 @@ def testServerInsecurePathRelative(self):
             rrq.options = {}
 
             # Start the download.
-            self.assertRaises(
-                tftpy.TftpException, serverstate.start, rrq.encode().buffer
-            )
+            with self.assertRaisesRegex(tftpy.TftpException, 'bad file path'):
+                serverstate.start(rrq.encode().buffer)
 
     def testServerInsecurePathRootSibling(self):
         raddress = "127.0.0.2"
@@ -456,9 +455,8 @@ def testServerInsecurePathRootSibling(self):
             rrq.options = {}
 
             # Start the download.
-            self.assertRaises(
-                tftpy.TftpException, serverstate.start, rrq.encode().buffer
-            )
+            with self.assertRaisesRegex(tftpy.TftpException, 'bad file path'):
+                serverstate.start(rrq.encode().buffer)
 
     def testServerSecurePathAbsolute(self):
         raddress = "127.0.0.2"
@@ -502,6 +500,27 @@ def testServerSecurePathRelative(self):
                 isinstance(serverstate.state, tftpy.TftpStates.TftpStateExpectACK)
             )
 
+    def testServerPathRoot(self):
+        raddress = "127.0.0.2"
+        rport = 10000
+        timeout = 5
+        with self.dummyServerDir() as d:
+            root = '/'
+            serverstate = tftpy.TftpContexts.TftpContextServer(
+                raddress, rport, timeout, root
+            )
+            rrq = tftpy.TftpPacketTypes.TftpPacketRRQ()
+            rrq.filename = os.path.join(os.path.abspath(d), "foo", "bar")
+            rrq.mode = "octet"
+            rrq.options = {}
+
+            # Start the download.
+            serverstate.start(rrq.encode().buffer)
+            # Should be in expectack state.
+            self.assertTrue(
+                isinstance(serverstate.state, tftpy.TftpStates.TftpStateExpectACK)
+            )
+
     def testServerDownloadWithStopNow(self, output="/tmp/out"):
         log.debug("===> Running testcase testServerDownloadWithStopNow")
         root = os.path.dirname(os.path.abspath(__file__))
diff --git a/tftpy/TftpStates.py b/tftpy/TftpStates.py
index dd217b6..cc7ee91 100644
--- a/tftpy/TftpStates.py
+++ b/tftpy/TftpStates.py
@@ -295,8 +295,11 @@ def serverInitial(self, pkt, raddress, rport):
         # (e.g. '..') and ensure that is still within the server's
         # root directory
         self.full_path = os.path.abspath(full_path)
-        log.debug("full_path is %s", full_path)
-        if self.full_path.startswith(os.path.normpath(self.context.root) + os.sep):
+        # Determine root path, replace double slashes with single
+        # // => /
+        root_path = (os.path.normpath(self.context.root) + os.sep).replace('//', '/')
+        log.debug("full_path is %s, server root is %s" % (self.full_path, root_path))
+        if self.full_path.startswith(root_path):
             log.info("requested file is in the server root - good")
         else:
             log.warning("requested file is not within the server root - bad")