diff --git a/windows/conpty.c b/windows/conpty.c
index f2882316..322af7bf 100644
--- a/windows/conpty.c
+++ b/windows/conpty.c
@@ -120,7 +120,8 @@ static size_t conpty_gotdata(
     }
 }
 
-static void conpty_sentdata(struct handle *h, size_t new_backlog, int err)
+static void conpty_sentdata(struct handle *h, size_t new_backlog, int err,
+                            bool close)
 {
     ConPTY *conpty = (ConPTY *)handle_get_privdata(h);
     if (err) {
diff --git a/windows/handle-io.c b/windows/handle-io.c
index 873eaf30..e012c8ed 100644
--- a/windows/handle-io.c
+++ b/windows/handle-io.c
@@ -284,6 +284,7 @@ struct handle_output {
      * drops.
      */
     handle_outputfn_t sentdata;
+    struct handle *sentdata_param;
 };
 
 static DWORD WINAPI handle_output_threadfunc(void *param)
@@ -361,7 +362,7 @@ static void handle_try_output(struct handle_output *ctx)
         ctx->busy = true;
     } else if (!ctx->busy && bufchain_size(&ctx->queued_data) == 0 &&
                ctx->outgoingeof == EOF_PENDING) {
-        CloseHandle(ctx->h);
+        ctx->sentdata(ctx->sentdata_param, 0, 0, true);
         ctx->h = INVALID_HANDLE_VALUE;
         ctx->outgoingeof = EOF_SENT;
     }
@@ -507,6 +508,7 @@ struct handle *handle_output_new(HANDLE handle, handle_outputfn_t sentdata,
     bufchain_init(&h->u.o.queued_data);
     h->u.o.outgoingeof = EOF_NO;
     h->u.o.sentdata = sentdata;
+    h->u.o.sentdata_param = h;
     h->u.o.flags = flags;
 
     ensure_ready_event_setup();
@@ -644,11 +646,11 @@ static void handle_ready(struct handle *h)
              * thread is terminating by now).
              */
             h->u.o.defunct = true;
-            h->u.o.sentdata(h, 0, h->u.o.writeerr);
+            h->u.o.sentdata(h, 0, h->u.o.writeerr, false);
         } else {
             bufchain_consume(&h->u.o.queued_data, h->u.o.lenwritten);
             noise_ultralight(NOISE_SOURCE_IOLEN, h->u.o.lenwritten);
-            h->u.o.sentdata(h, bufchain_size(&h->u.o.queued_data), 0);
+            h->u.o.sentdata(h, bufchain_size(&h->u.o.queued_data), 0, false);
             handle_try_output(&h->u.o);
         }
         break;
diff --git a/windows/handle-socket.c b/windows/handle-socket.c
index dbc4e0de..a024807e 100644
--- a/windows/handle-socket.c
+++ b/windows/handle-socket.c
@@ -93,10 +93,19 @@ static size_t handle_stderr(
     return 0;
 }
 
-static void handle_sentdata(struct handle *h, size_t new_backlog, int err)
+static void handle_sentdata(struct handle *h, size_t new_backlog, int err,
+                            bool close)
 {
     HandleSocket *hs = (HandleSocket *)handle_get_privdata(h);
 
+    if (close) {
+        if (hs->send_H != INVALID_HANDLE_VALUE)
+            CloseHandle(hs->send_H);
+        if (hs->recv_H != INVALID_HANDLE_VALUE && hs->recv_H != hs->send_H)
+            CloseHandle(hs->recv_H);
+        hs->send_H = hs->recv_H = INVALID_HANDLE_VALUE;
+    }
+
     if (err) {
         plug_closing(hs->plug, win_strerror(err), err, 0);
         return;
@@ -125,8 +134,9 @@ static void sk_handle_close(Socket *s)
 
     handle_free(hs->send_h);
     handle_free(hs->recv_h);
-    CloseHandle(hs->send_H);
-    if (hs->recv_H != hs->send_H)
+    if (hs->send_H != INVALID_HANDLE_VALUE)
+        CloseHandle(hs->send_H);
+    if (hs->recv_H != INVALID_HANDLE_VALUE && hs->recv_H != hs->send_H)
         CloseHandle(hs->recv_H);
     bufchain_clear(&hs->inputdata);
 
diff --git a/windows/platform.h b/windows/platform.h
index ba07ea1a..65dacdc1 100644
--- a/windows/platform.h
+++ b/windows/platform.h
@@ -615,7 +615,7 @@ struct handle;
 typedef size_t (*handle_inputfn_t)(
     struct handle *h, const void *data, size_t len, int err);
 typedef void (*handle_outputfn_t)(
-    struct handle *h, size_t new_backlog, int err);
+    struct handle *h, size_t new_backlog, int err, bool close);
 struct handle *handle_input_new(HANDLE handle, handle_inputfn_t gotdata,
                                 void *privdata, int flags);
 struct handle *handle_output_new(HANDLE handle, handle_outputfn_t sentdata,
diff --git a/windows/plink.c b/windows/plink.c
index 8d3a75cf..503ae30b 100644
--- a/windows/plink.c
+++ b/windows/plink.c
@@ -216,8 +216,14 @@ size_t stdin_gotdata(struct handle *h, const void *data, size_t len, int err)
         return 0;
 }
 
-void stdouterr_sent(struct handle *h, size_t new_backlog, int err)
+void stdouterr_sent(struct handle *h, size_t new_backlog, int err, bool close)
 {
+    if (close) {
+        CloseHandle(outhandle);
+        CloseHandle(errhandle);
+        outhandle = errhandle = INVALID_HANDLE_VALUE;
+    }
+
     if (err) {
         char buf[4096];
         FormatMessage(FORMAT_MESSAGE_FROM_SYSTEM, NULL, err, 0,
diff --git a/windows/serial.c b/windows/serial.c
index 470c979f..d966145c 100644
--- a/windows/serial.c
+++ b/windows/serial.c
@@ -73,7 +73,8 @@ static size_t serial_gotdata(
     }
 }
 
-static void serial_sentdata(struct handle *h, size_t new_backlog, int err)
+static void serial_sentdata(struct handle *h, size_t new_backlog, int err,
+                            bool close)
 {
     Serial *serial = (Serial *)handle_get_privdata(h);
     if (err) {