diff --git a/src/chat.c b/src/chat.c
index 8c72ae0..8cec8de 100644
--- a/src/chat.c
+++ b/src/chat.c
@@ -123,7 +123,7 @@ static void chat_onFileSendRequest(ToxWindow *self, Tox *m, int num, uint8_t fil
     wprintw(ctx->history, "File transfer request for '%s' (%llu bytes).\n", filename, 
             (long long unsigned int)filesize);
 
-    if (filenum >= MAX_FILENUMBER) {
+    if (filenum >= MAX_FILES) {
         wprintw(ctx->history, "Too many pending file requests; discarding.\n");
         return;
     }
@@ -142,7 +142,7 @@ static void chat_onFileSendRequest(ToxWindow *self, Tox *m, int num, uint8_t fil
 
     wprintw(ctx->history, "Type '/savefile %d' to accept the file transfer.\n", filenum);
 
-    friends[num].file_receiver.pending_file_transfers[filenum] = num;
+    friends[num].file_receiver.pending[filenum] = true;
     strcpy(friends[num].file_receiver.filenames[filenum], filename);
 
     self->blink = true;
@@ -221,6 +221,11 @@ static void chat_groupinvite(ToxWindow *self, ChatContext *ctx, Tox *m, uint8_t
 
 static void chat_sendfile(ToxWindow *self, ChatContext *ctx, Tox *m, uint8_t *path)
 {
+    if (num_file_senders >= MAX_FILES) {
+        wprintw(ctx->history,"Please wait for some of your outgoing file transfers to complete.\n");
+        return;
+    }
+
     int path_len = strlen(path);
 
     if (path_len > MAX_STR_SIZE) {
@@ -250,34 +255,53 @@ static void chat_sendfile(ToxWindow *self, ChatContext *ctx, Tox *m, uint8_t *pa
         return;
     }
 
-    memcpy(file_senders[num_file_senders].pathname, path, path_len + 1);
-    file_senders[num_file_senders].chatwin = ctx->history;
-    file_senders[num_file_senders].file = file_to_send;
-    file_senders[num_file_senders].filenum = (uint8_t) filenum;
-    file_senders[num_file_senders].friendnum = friendnum;
-    file_senders[num_file_senders].piecelen = fread(file_senders[num_file_senders].nextpiece, 1,
-                                                    tox_filedata_size(m, friendnum), file_to_send);
+    int i;
 
-    wprintw(ctx->history, "Sending file '%s'...\n", path);
-    ++num_file_senders;
+    for (i = 0; i < MAX_FILES; ++i) {
+        if (!file_senders[i].active) {
+            memcpy(file_senders[i].pathname, path, path_len + 1);
+            file_senders[i].active = true;
+            file_senders[i].chatwin = ctx->history;
+            file_senders[i].file = file_to_send;
+            file_senders[i].filenum = (uint8_t) filenum;
+            file_senders[i].friendnum = friendnum;
+            file_senders[i].piecelen = fread(file_senders[i].nextpiece, 1,
+                                             tox_filedata_size(m, friendnum), file_to_send);
+
+            wprintw(ctx->history, "Sending file: '%s'\n", path);
+
+            if (i == num_file_senders)
+                ++num_file_senders;
+
+            return;
+        }
+    }
 }
 
 static void chat_savefile(ToxWindow *self, ChatContext *ctx, Tox *m, uint8_t *num)
 {
     uint8_t filenum = atoi(num);
 
-    if (filenum < 0 || filenum >= MAX_FILENUMBER) {
-        wprintw(ctx->history, "File transfer failed.\n");
+    if (filenum < 0 || filenum >= MAX_FILES) {
+        wprintw(ctx->history, "No pending file transfers with that number.\n");
         return;
     }
 
     int friendnum = self->num;
+
+    if (!friends[friendnum].file_receiver.pending[filenum]) {
+        wprintw(ctx->history, "No pending file transfers with that number.\n");
+        return;
+    }
+
     uint8_t *filename = friends[friendnum].file_receiver.filenames[filenum];
 
     if (tox_file_sendcontrol(m, friendnum, 1, filenum, TOX_FILECONTROL_ACCEPT, 0, 0))
         wprintw(ctx->history, "Accepted file transfer %u. Saving file as: '%s'\n", filenum, filename);
     else
         wprintw(ctx->history, "File transfer failed.\n");
+
+    friends[friendnum].file_receiver.pending[filenum] = false;
 }
 
 static void print_chat_help(ChatContext *ctx)
diff --git a/src/main.c b/src/main.c
index 49daee0..ccc7263 100644
--- a/src/main.c
+++ b/src/main.c
@@ -351,7 +351,7 @@ void do_file_senders(Tox *m)
 {
     int i;
 
-    for (i = 0; i < NUM_FILE_SENDERS; ++i) {
+    for (i = 0; i < MAX_FILES; ++i) {
         if (file_senders[i].file == NULL)
             continue;
 
@@ -368,13 +368,21 @@ void do_file_senders(Tox *m)
 
             if (file_senders[i].piecelen == 0) {
                 fclose(file_senders[i].file);
-                file_senders[i].file = NULL;
-                tox_file_sendcontrol(m, friendnum, 0, filenum, 
-                                     TOX_FILECONTROL_FINISHED, 0, 0);
+                memset(&file_senders[i], 0, sizeof(FileSender));
+
+                tox_file_sendcontrol(m, friendnum, 0, filenum, TOX_FILECONTROL_FINISHED, 0, 0);
 
                 uint8_t *pathname = file_senders[i].pathname;
-
                 wprintw(file_senders[i].chatwin, "File '%s' successfuly sent.\n", pathname);
+
+                int i;
+
+                for (i = num_file_senders; i > 0; --i) {
+                    if (file_senders[i-1].active)
+                        break;
+                }
+
+                num_file_senders = i;
                 return;
             }
         }
diff --git a/src/toxic_windows.h b/src/toxic_windows.h
index 2a0d4ef..22f9554 100644
--- a/src/toxic_windows.h
+++ b/src/toxic_windows.h
@@ -97,26 +97,26 @@ typedef struct {
 
 /* Start file transfer code */
 
-#define NUM_FILE_SENDERS 256
-#define MAX_FILENUMBER 100
+#define MAX_FILES 256
 #define FILE_PIECE_SIZE 1024
 
 typedef struct {
     FILE *file;
     WINDOW *chatwin;
     int friendnum;
+    bool active;
     uint8_t filenum;
     uint8_t nextpiece[FILE_PIECE_SIZE];
     uint16_t piecelen;
     uint8_t pathname[MAX_STR_SIZE];
 } FileSender;
 
-FileSender file_senders[NUM_FILE_SENDERS];
+FileSender file_senders[MAX_FILES];
 uint8_t num_file_senders;
 
 typedef struct {
-  uint8_t pending_file_transfers[MAX_FILENUMBER];
-  uint8_t filenames[MAX_FILENUMBER][MAX_STR_SIZE];
+  uint8_t filenames[MAX_FILES][MAX_STR_SIZE];
+  bool pending[MAX_FILES];
 } FileReceiver;
 
 /* End file transfer code */