diff --git a/src/core/iomgr/iocp_windows.c b/src/core/iomgr/iocp_windows.c
index e7fc744ceb8a7be7ecee2de88bb095abd70fdbe1..1cdf3da0d6258338449a32477ec2ecd610adb67f 100644
--- a/src/core/iomgr/iocp_windows.c
+++ b/src/core/iomgr/iocp_windows.c
@@ -177,6 +177,10 @@ void grpc_iocp_socket_orphan(grpc_winsocket *socket) {
   socket->orphan = 1;
 }
 
+/* Calling notify_on_read or write means either of two things:
+   -) The IOCP already completed in the background, and we need to call
+   the callback now.
+   -) The IOCP hasn't completed yet, and we're queuing it for later. */
 static void socket_notify_on_iocp(grpc_winsocket *socket,
                                   void(*cb)(void *, int), void *opaque,
                                   grpc_winsocket_callback_info *info) {
diff --git a/src/core/iomgr/iomgr_windows.c b/src/core/iomgr/iomgr_windows.c
index f130ab9a078ead0ef81fd3ef68b2ef53d2b4eee0..74cd5a829b28d4be850cbc50fadba9cb333d5d18 100644
--- a/src/core/iomgr/iomgr_windows.c
+++ b/src/core/iomgr/iomgr_windows.c
@@ -43,6 +43,10 @@
 #include "src/core/iomgr/iocp_windows.h"
 #include "src/core/iomgr/iomgr.h"
 
+/* Windows' io manager is going to be fully designed using IO completion
+   ports. All of what we're doing here is basically make sure that
+   Windows sockets are initialized in and out. */
+
 static void winsock_init(void) {
   WSADATA wsaData;
   int status = WSAStartup(MAKEWORD(2, 0), &wsaData);
diff --git a/src/core/iomgr/pollset_kick_windows.h b/src/core/iomgr/pollset_kick_windows.h
index 3836aa00820a046d966a073c2bf2636dce68b3ef..c675c119aba0185026e2bb72259658ee73110222 100644
--- a/src/core/iomgr/pollset_kick_windows.h
+++ b/src/core/iomgr/pollset_kick_windows.h
@@ -36,6 +36,9 @@
 
 #include <grpc/support/sync.h>
 
+/* There isn't really any such thing as a pollset under Windows, due to the
+   nature of the IO completion ports. */
+
 struct grpc_kick_fd_info;
 
 typedef struct grpc_pollset_kick_state {
diff --git a/src/core/iomgr/pollset_windows.c b/src/core/iomgr/pollset_windows.c
index bea67116116feccd94a9101ea6fc06f66ccf2ea8..5af0685f9d97818dee8255028af3db176155174f 100644
--- a/src/core/iomgr/pollset_windows.c
+++ b/src/core/iomgr/pollset_windows.c
@@ -41,6 +41,11 @@
 #include "src/core/iomgr/iomgr_internal.h"
 #include "src/core/iomgr/pollset_windows.h"
 
+/* There isn't really any such thing as a pollset under Windows, due to the
+   nature of the IO completion ports. We're still going to provide a minimal
+   set of features for the sake of the rest of grpc. But grpc_pollset_work
+   won't actually do any polling, and return as quickly as possible. */
+
 void grpc_pollset_init(grpc_pollset *pollset) {
   gpr_mu_init(&pollset->mu);
   gpr_cv_init(&pollset->cv);
diff --git a/src/core/iomgr/pollset_windows.h b/src/core/iomgr/pollset_windows.h
index 266175abfb91816954dd30f87c2fd88eac67f119..e1115bac4ff0fc74425c451f59caa8f07f761aa3 100644
--- a/src/core/iomgr/pollset_windows.h
+++ b/src/core/iomgr/pollset_windows.h
@@ -40,10 +40,10 @@
 #include "src/core/iomgr/pollset_kick.h"
 #include "src/core/iomgr/socket_windows.h"
 
-/* forward declare only in this file to avoid leaking impl details via
-   pollset.h; real users of grpc_fd should always include 'fd_posix.h' and not
-   use the struct tag */
-struct grpc_fd;
+/* There isn't really any such thing as a pollset under Windows, due to the
+   nature of the IO completion ports. A Windows "pollset" is merely a mutex
+   and a condition variable, as this is the minimal set of features we need
+   implemented for the rest of grpc. But we won't use them directly. */
 
 typedef struct grpc_pollset {
   gpr_mu mu;
diff --git a/src/core/iomgr/socket_windows.c b/src/core/iomgr/socket_windows.c
index fe0196d99cdae120ea88982ae969c74c744c7e0a..9306310d435ba5f5b6e5aaf2f2c2415a4f8aca96 100644
--- a/src/core/iomgr/socket_windows.c
+++ b/src/core/iomgr/socket_windows.c
@@ -41,9 +41,9 @@
 #include "src/core/iomgr/iocp_windows.h"
 #include "src/core/iomgr/iomgr.h"
 #include "src/core/iomgr/iomgr_internal.h"
-#include "src/core/iomgr/socket_windows.h"
 #include "src/core/iomgr/pollset.h"
 #include "src/core/iomgr/pollset_windows.h"
+#include "src/core/iomgr/socket_windows.h"
 
 grpc_winsocket *grpc_winsocket_create(SOCKET socket) {
   grpc_winsocket *r = gpr_malloc(sizeof(grpc_winsocket));
@@ -55,16 +55,29 @@ grpc_winsocket *grpc_winsocket_create(SOCKET socket) {
   return r;
 }
 
-static void shutdown_op(grpc_winsocket_callback_info *info) {
-  if (!info->cb) return;
-  grpc_iomgr_add_delayed_callback(info->cb, info->opaque, 0);
-}
-
+/* Schedule a shutdown of the socket operations. Will call the pending
+   operations to abort them. We need to do that this way because of the
+   various callsites of that function, which happens to be in various
+   mutex hold states, and that'd be unsafe to call them directly. */
 void grpc_winsocket_shutdown(grpc_winsocket *socket) {
-  shutdown_op(&socket->read_info);
-  shutdown_op(&socket->write_info);
+  gpr_mu_lock(&socket->state_mu);
+  if (socket->read_info.cb) {
+    grpc_iomgr_add_delayed_callback(socket->read_info.cb,
+                                    socket->read_info.opaque, 0);
+  }
+  if (socket->write_info.cb) {
+    grpc_iomgr_add_delayed_callback(socket->write_info.cb,
+                                    socket->write_info.opaque, 0);
+  }
+  gpr_mu_unlock(&socket->state_mu);
 }
 
+/* Abandons a socket. Either we're going to queue it up for garbage collecting
+   from the IO Completion Port thread, or destroy it immediately. Note that this
+   mechanisms assumes that we're either always waiting for an operation, or we
+   explicitely know that we don't. If there is a future case where we can have
+   an "idle" socket which is neither trying to read or write, we'd start leaking
+   both memory and sockets. */
 void grpc_winsocket_orphan(grpc_winsocket *winsocket) {
   SOCKET socket = winsocket->socket;
   if (!winsocket->closed_early) {
diff --git a/src/core/iomgr/socket_windows.h b/src/core/iomgr/socket_windows.h
index ee090668ea75f7bfd8f2c4ca9aec13070d59b89e..6e778a776a3bbc43003e3b199a0bc0ec78e2e8fd 100644
--- a/src/core/iomgr/socket_windows.h
+++ b/src/core/iomgr/socket_windows.h
@@ -39,21 +39,43 @@
 #include <grpc/support/sync.h>
 #include <grpc/support/atm.h>
 
+/* This holds the data for an outstanding read or write on a socket.
+   The mutex to protect the concurrent access to that data is the one
+   inside the winsocket wrapper. */
 typedef struct grpc_winsocket_callback_info {
   /* This is supposed to be a WSAOVERLAPPED, but in order to get that
-   * definition, we need to include ws2tcpip.h, which needs to be included
-   * from the top, otherwise it'll clash with a previous inclusion of
-   * windows.h that in turns includes winsock.h. If anyone knows a way
-   * to do it properly, feel free to send a patch.
-   */
+     definition, we need to include ws2tcpip.h, which needs to be included
+     from the top, otherwise it'll clash with a previous inclusion of
+     windows.h that in turns includes winsock.h. If anyone knows a way
+     to do it properly, feel free to send a patch. */
   OVERLAPPED overlapped;
+  /* The callback information for the pending operation. May be empty if the
+     caller hasn't registered a callback yet. */
   void(*cb)(void *opaque, int success);
   void *opaque;
+  /* A boolean to describe if the IO Completion Port got a notification for
+     that operation. This will happen if the operation completed before the
+     called had time to register a callback. We could avoid that behavior
+     altogether by forcing the caller to always register its callback before
+     proceeding queue an operation, but it is frequent for an IO Completion
+     Port to trigger quickly. This way we avoid a context switch for calling
+     the callback. We also simplify the read / write operations to avoid having
+     to hold a mutex for a long amount of time. */
   int has_pending_iocp;
+  /* The results of the overlapped operation. */
   DWORD bytes_transfered;
   int wsa_error;
 } grpc_winsocket_callback_info;
 
+/* This is a wrapper to a Windows socket. A socket can have one outstanding
+   read, and one outstanding write. Doing an asynchronous accept means waiting
+   for a read operation. Doing an asynchronous connect means waiting for a
+   write operation. These are completely abitrary ties between the operation
+   and the kind of event, because we can have one overlapped per pending
+   operation, whichever its nature is. So we could have more dedicated pending
+   operation callbacks for connect and listen. But given the scope of listen
+   and accept, we don't need to go to that extent and waste memory. Also, this
+   is closer to what happens in posix world. */
 typedef struct grpc_winsocket {
   SOCKET socket;
 
@@ -62,17 +84,35 @@ typedef struct grpc_winsocket {
 
   gpr_mu state_mu;
 
+  /* You can't add the same socket twice to the same IO Completion Port.
+     This prevents that. */
   int added_to_iocp;
+  /* A boolean to indicate that the caller has abandonned that socket, but
+     there is a pending operation that the IO Completion Port will have to
+     wait for. The socket will be collected at that time. */
   int orphan;
+  /* A boolean to indicate that the socket was already closed somehow, and
+     that no operation is going to be pending. Trying to abandon a socket in
+     that state won't result in an orphan, but will instead be destroyed
+     without further delay. We could avoid that boolean by adding one into
+     grpc_winsocket_callback_info describing that the operation is pending,
+     but that 1) waste memory more and 2) obfuscate the intent a bit more. */
   int closed_early;
 } grpc_winsocket;
 
-/* Create a wrapped windows handle.
-This takes ownership of closing it. */
+/* Create a wrapped windows handle. This takes ownership of it, meaning that
+   it will be responsible for closing it. */
 grpc_winsocket *grpc_winsocket_create(SOCKET socket);
 
+/* Initiate an asynchronous shutdown of the socket. Will call off any pending
+   operation to cancel them. */
 void grpc_winsocket_shutdown(grpc_winsocket *socket);
+
+/* Abandon a socket. */
 void grpc_winsocket_orphan(grpc_winsocket *socket);
+
+/* Destroy a socket. Should only be called by the IO Completion Port thread,
+   or by grpc_winsocket_orphan if there's no pending operation. */
 void grpc_winsocket_destroy(grpc_winsocket *socket);
 
 #endif  /* GRPC_INTERNAL_CORE_IOMGR_SOCKET_WINDOWS_H */
diff --git a/src/core/iomgr/tcp_server_windows.c b/src/core/iomgr/tcp_server_windows.c
index c4d3293e83a824995f6fa2425933ae5f7d47b7d2..c6137e1e1d635fd653bcd1e52516126285a0d599 100644
--- a/src/core/iomgr/tcp_server_windows.c
+++ b/src/core/iomgr/tcp_server_windows.c
@@ -109,7 +109,8 @@ void grpc_tcp_server_destroy(grpc_tcp_server *s,
   /* First, shutdown all fd's. This will queue abortion calls for all
      of the pending accepts. */
   for (i = 0; i < s->nports; i++) {
-    grpc_winsocket_shutdown(s->ports[i].socket);
+    server_port *sp = &s->ports[i];
+    grpc_winsocket_shutdown(sp->socket);
   }
   /* This happens asynchronously. Wait while that happens. */
   while (s->active_ports) {
@@ -275,22 +276,28 @@ static void on_accept(void *arg, int from_iocp) {
     /* If we're not notified from the IOCP, it means we are asked to shutdown.
        This will initiate that shutdown. Calling closesocket will trigger an
        IOCP notification, that will call this function a second time, from
-       the IOCP thread. */
+       the IOCP thread. Of course, this only works if the socket was, in fact,
+       listening. If that's not the case, we'd wait indefinitely. That's a bit
+       of a degenerate case, but it can happen if you create a server, but
+       don't start it. So let's support that by recursing once. */
     sp->shutting_down = 1;
     sp->new_socket = INVALID_SOCKET;
-    closesocket(sock);
+    if (sock != INVALID_SOCKET) {
+      closesocket(sock);
+    } else {
+      on_accept(sp, 1);
+    }
+    return;
   }
 
   /* The only time we should call our callback, is where we successfully
      managed to accept a connection, and created an endpoint. */
   if (ep) sp->server->cb(sp->server->cb_arg, ep);
-  if (from_iocp) {
-    /* As we were notified from the IOCP of one and exactly one accept,
-       the former socked we created has now either been destroy or assigned
-       to the new connection. We need to create a new one for the next
-       connection. */
-    start_accept(sp);
-  }
+  /* As we were notified from the IOCP of one and exactly one accept,
+      the former socked we created has now either been destroy or assigned
+      to the new connection. We need to create a new one for the next
+      connection. */
+  start_accept(sp);
 }
 
 static int add_socket_to_server(grpc_tcp_server *s, SOCKET sock,
@@ -332,6 +339,7 @@ static int add_socket_to_server(grpc_tcp_server *s, SOCKET sock,
     sp->socket = grpc_winsocket_create(sock);
     sp->shutting_down = 0;
     sp->AcceptEx = AcceptEx;
+    sp->new_socket = INVALID_SOCKET;
     GPR_ASSERT(sp->socket);
     gpr_mu_unlock(&s->mu);
   }
diff --git a/src/core/iomgr/tcp_windows.c b/src/core/iomgr/tcp_windows.c
index d5b06e7b0b235432e08fae6008bea7d91e6347ba..c8483bd891cbe73aac0a1faa9e0fe6fe04413b51 100644
--- a/src/core/iomgr/tcp_windows.c
+++ b/src/core/iomgr/tcp_windows.c
@@ -76,8 +76,11 @@ int grpc_tcp_prepare_socket(SOCKET sock) {
 }
 
 typedef struct grpc_tcp {
+  /* This is our C++ class derivation emulation. */
   grpc_endpoint base;
+  /* The one socket this endpoint is using. */
   grpc_winsocket *socket;
+  /* Refcounting how many operations are in progress. */
   gpr_refcount refcount;
 
   grpc_endpoint_read_cb read_cb;
@@ -90,6 +93,10 @@ typedef struct grpc_tcp {
   gpr_slice_buffer write_slices;
   int outstanding_write;
 
+  /* The IO Completion Port runs from another thread. We need some mechanism
+     to protect ourselves when requesting a shutdown. */
+  gpr_mu mu;
+  int shutting_down;
 } grpc_tcp;
 
 static void tcp_ref(grpc_tcp *tcp) {
@@ -100,11 +107,13 @@ static void tcp_unref(grpc_tcp *tcp) {
   if (gpr_unref(&tcp->refcount)) {
     gpr_slice_buffer_destroy(&tcp->write_slices);
     grpc_winsocket_orphan(tcp->socket);
+    gpr_mu_destroy(&tcp->mu);
     gpr_free(tcp);
   }
 }
 
-static void on_read(void *tcpp, int success) {
+/* Asynchronous callback from the IOCP, or the background thread. */
+static void on_read(void *tcpp, int from_iocp) {
   grpc_tcp *tcp = (grpc_tcp *) tcpp;
   grpc_winsocket *socket = tcp->socket;
   gpr_slice sub;
@@ -114,16 +123,25 @@ static void on_read(void *tcpp, int success) {
   grpc_endpoint_read_cb cb = tcp->read_cb;
   grpc_winsocket_callback_info *info = &socket->read_info;
   void *opaque = tcp->read_user_data;
+  int do_abort = 0;
+
+  gpr_mu_lock(&tcp->mu);
+  if (!from_iocp || tcp->shutting_down) {
+    /* If we are here with from_iocp set to true, it means we got raced to
+    shutting down the endpoint. No actual abort callback will happen
+    though, so we're going to do it from here. */
+    do_abort = 1;
+  }
+  gpr_mu_unlock(&tcp->mu);
 
-  GPR_ASSERT(tcp->outstanding_read);
-
-  if (!success) {
+  if (do_abort) {
+    if (from_iocp) gpr_slice_unref(tcp->read_slice);
     tcp_unref(tcp);
     cb(opaque, NULL, 0, GRPC_ENDPOINT_CB_SHUTDOWN);
     return;
   }
 
-  tcp->outstanding_read = 0;
+  GPR_ASSERT(tcp->outstanding_read);
 
   if (socket->read_info.wsa_error != 0) {
     char *utf8_message = gpr_format_message(info->wsa_error);
@@ -142,6 +160,9 @@ static void on_read(void *tcpp, int success) {
       status = GRPC_ENDPOINT_CB_EOF;
     }
   }
+
+  tcp->outstanding_read = 0;
+
   tcp_unref(tcp);
   cb(opaque, slice, nslices, status);
 }
@@ -158,6 +179,7 @@ static void win_notify_on_read(grpc_endpoint *ep,
   WSABUF buffer;
 
   GPR_ASSERT(!tcp->outstanding_read);
+  GPR_ASSERT(!tcp->shutting_down);
   tcp_ref(tcp);
   tcp->outstanding_read = 1;
   tcp->read_cb = cb;
@@ -168,10 +190,12 @@ static void win_notify_on_read(grpc_endpoint *ep,
   buffer.len = GPR_SLICE_LENGTH(tcp->read_slice);
   buffer.buf = (char *)GPR_SLICE_START_PTR(tcp->read_slice);
 
+  /* First let's try a synchronous, non-blocking read. */
   status = WSARecv(tcp->socket->socket, &buffer, 1, &bytes_read, &flags,
                    NULL, NULL);
   info->wsa_error = status == 0 ? 0 : WSAGetLastError();
 
+  /* Did we get data immediately ? Yay. */
   if (info->wsa_error != WSAEWOULDBLOCK) {
     info->bytes_transfered = bytes_read;
     /* This might heavily recurse. */
@@ -179,6 +203,7 @@ static void win_notify_on_read(grpc_endpoint *ep,
     return;
   }
 
+  /* Otherwise, let's retry, by queuing a read. */
   memset(&tcp->socket->read_info.overlapped, 0, sizeof(OVERLAPPED));
   status = WSARecv(tcp->socket->socket, &buffer, 1, &bytes_read, &flags,
                    &info->overlapped, NULL);
@@ -192,30 +217,53 @@ static void win_notify_on_read(grpc_endpoint *ep,
 
   if (error != WSA_IO_PENDING) {
     char *utf8_message = gpr_format_message(WSAGetLastError());
-    __debugbreak();
-    gpr_log(GPR_ERROR, "WSARecv error: %s", utf8_message);
+    gpr_log(GPR_ERROR, "WSARecv error: %s - this means we're going to leak.",
+            utf8_message);
     gpr_free(utf8_message);
-    /* would the IO completion port be called anyway... ? Let's assume not. */
+    /* I'm pretty sure this is a very bad situation there. Hence the log.
+       What will happen now is that the socket will neither wait for read
+       or write, unless the caller retry, which is unlikely, but I am not
+       sure if that's guaranteed. And there might also be a write pending.
+       This means that the future orphanage of that socket will be in limbo,
+       and we're going to leak it. I have no idea what could cause this
+       specific case however, aside from a parameter error from our call.
+       Normal read errors would actually happen during the overlapped
+       operation, which is the supported way to go for that. */
     tcp->outstanding_read = 0;
     tcp_unref(tcp);
     cb(arg, NULL, 0, GRPC_ENDPOINT_CB_ERROR);
+    /* Per the comment above, I'm going to treat that case as a hard failure
+       for now, and leave the option to catch that and debug. */
+    __debugbreak();
     return;
   }
 
   grpc_socket_notify_on_read(tcp->socket, on_read, tcp);
 }
 
-static void on_write(void *tcpp, int success) {
+/* Asynchronous callback from the IOCP, or the background thread. */
+static void on_write(void *tcpp, int from_iocp) {
   grpc_tcp *tcp = (grpc_tcp *) tcpp;
   grpc_winsocket *handle = tcp->socket;
   grpc_winsocket_callback_info *info = &handle->write_info;
   grpc_endpoint_cb_status status = GRPC_ENDPOINT_CB_OK;
   grpc_endpoint_write_cb cb = tcp->write_cb;
   void *opaque = tcp->write_user_data;
+  int do_abort = 0;
+
+  gpr_mu_lock(&tcp->mu);
+  if (!from_iocp || tcp->shutting_down) {
+    /* If we are here with from_iocp set to true, it means we got raced to
+        shutting down the endpoint. No actual abort callback will happen
+        though, so we're going to do it from here. */
+    do_abort = 1;
+  }
+  gpr_mu_unlock(&tcp->mu);
 
   GPR_ASSERT(tcp->outstanding_write);
 
-  if (!success) {
+  if (do_abort) {
+    if (from_iocp) gpr_slice_buffer_reset_and_unref(&tcp->write_slices);
     tcp_unref(tcp);
     cb(opaque, GRPC_ENDPOINT_CB_SHUTDOWN);
     return;
@@ -238,6 +286,7 @@ static void on_write(void *tcpp, int success) {
   cb(opaque, status);
 }
 
+/* Initiates a write. */
 static grpc_endpoint_write_status win_write(grpc_endpoint *ep,
                                             gpr_slice *slices, size_t nslices,
                                             grpc_endpoint_write_cb cb,
@@ -253,11 +302,13 @@ static grpc_endpoint_write_status win_write(grpc_endpoint *ep,
   WSABUF *buffers = local_buffers;
 
   GPR_ASSERT(!tcp->outstanding_write);
+  GPR_ASSERT(!tcp->shutting_down);
   tcp_ref(tcp);
 
   tcp->outstanding_write = 1;
   tcp->write_cb = cb;
   tcp->write_user_data = arg;
+
   gpr_slice_buffer_addn(&tcp->write_slices, slices, nslices);
 
   if (tcp->write_slices.count > GPR_ARRAY_SIZE(local_buffers)) {
@@ -270,10 +321,14 @@ static grpc_endpoint_write_status win_write(grpc_endpoint *ep,
     buffers[i].buf = (char *)GPR_SLICE_START_PTR(tcp->write_slices.slices[i]);
   }
 
+  /* First, let's try a synchronous, non-blocking write. */
   status = WSASend(socket->socket, buffers, tcp->write_slices.count,
                    &bytes_sent, 0, NULL, NULL);
   info->wsa_error = status == 0 ? 0 : WSAGetLastError();
 
+  /* We would kind of expect to get a WSAEWOULDBLOCK here, especially on a busy
+     connection that has its send queue filled up. But if we don't, then we can
+     avoid doing an async write operation at all. */
   if (info->wsa_error != WSAEWOULDBLOCK) {
     grpc_endpoint_write_status ret = GRPC_ENDPOINT_WRITE_ERROR;
     if (status == 0) {
@@ -291,25 +346,42 @@ static grpc_endpoint_write_status win_write(grpc_endpoint *ep,
     return ret;
   }
 
+  /* If we got a WSAEWOULDBLOCK earlier, then we need to re-do the same
+     operation, this time asynchronously. */
   memset(&socket->write_info.overlapped, 0, sizeof(OVERLAPPED));
   status = WSASend(socket->socket, buffers, tcp->write_slices.count,
                    &bytes_sent, 0, &socket->write_info.overlapped, NULL);
   if (allocated) gpr_free(allocated);
 
+  /* It is possible the operation completed then. But we'd still get an IOCP
+     notification. So let's ignore it and wait for the IOCP. */
   if (status != 0) {
     int error = WSAGetLastError();
     if (error != WSA_IO_PENDING) {
       char *utf8_message = gpr_format_message(WSAGetLastError());
-      __debugbreak();
-      gpr_log(GPR_ERROR, "WSASend error: %s", utf8_message);
+      gpr_log(GPR_ERROR, "WSASend error: %s - this means we're going to leak.",
+              utf8_message);
       gpr_free(utf8_message);
-      /* would the IO completion port be called anyway ? Let's assume not. */
+    /* I'm pretty sure this is a very bad situation there. Hence the log.
+       What will happen now is that the socket will neither wait for read
+       or write, unless the caller retry, which is unlikely, but I am not
+       sure if that's guaranteed. And there might also be a read pending.
+       This means that the future orphanage of that socket will be in limbo,
+       and we're going to leak it. I have no idea what could cause this
+       specific case however, aside from a parameter error from our call.
+       Normal read errors would actually happen during the overlapped
+       operation, which is the supported way to go for that. */
       tcp->outstanding_write = 0;
       tcp_unref(tcp);
+      /* Per the comment above, I'm going to treat that case as a hard failure
+         for now, and leave the option to catch that and debug. */
+      __debugbreak();
       return GRPC_ENDPOINT_WRITE_ERROR;
     }
   }
 
+  /* As all is now setup, we can now ask for the IOCP notification. It may
+     trigger the callback immediately however, but no matter. */
   grpc_socket_notify_on_write(socket, on_write, tcp);
   return GRPC_ENDPOINT_WRITE_PENDING;
 }
@@ -319,9 +391,20 @@ static void win_add_to_pollset(grpc_endpoint *ep, grpc_pollset *pollset) {
   grpc_iocp_add_socket(tcp->socket);
 }
 
+/* Initiates a shutdown of the TCP endpoint. This will queue abort callbacks
+   for the potential read and write operations. It is up to the caller to
+   guarantee this isn't called in parallel to a read or write request, so
+   we're not going to protect against these. However the IO Completion Port
+   callback will happen from another thread, so we need to protect against
+   concurrent access of the data structure in that regard. */
 static void win_shutdown(grpc_endpoint *ep) {
   grpc_tcp *tcp = (grpc_tcp *) ep;
+  gpr_mu_lock(&tcp->mu);
+  /* At that point, what may happen is that we're already inside the IOCP
+     callback. See the comments in on_read and on_write. */
+  tcp->shutting_down = 1;
   grpc_winsocket_shutdown(tcp->socket);
+  gpr_mu_unlock(&tcp->mu);
 }
 
 static void win_destroy(grpc_endpoint *ep) {
@@ -338,6 +421,7 @@ grpc_endpoint *grpc_tcp_create(grpc_winsocket *socket) {
   memset(tcp, 0, sizeof(grpc_tcp));
   tcp->base.vtable = &vtable;
   tcp->socket = socket;
+  gpr_mu_init(&tcp->mu);
   gpr_slice_buffer_init(&tcp->write_slices);
   gpr_ref_init(&tcp->refcount, 1);
   return &tcp->base;