diff --git a/src/command/cmd_funcs.c b/src/command/cmd_funcs.c
index 23f0b98d..d16cd938 100644
--- a/src/command/cmd_funcs.c
+++ b/src/command/cmd_funcs.c
@@ -95,6 +95,12 @@
 #ifdef HAVE_OMEMO
 #include "omemo/omemo.h"
 #include "xmpp/omemo.h"
+
+#define AESGCM_URL_SCHEME "aesgcm"
+#define AESGCM_URL_NONCE_LEN 24
+#define AESGCM_URL_KEY_LEN 64
+#define AESGCM_URL_FRAGMENT_LEN                                                \
+  (size_t)(AESGCM_URL_NONCE_LEN + AESGCM_URL_KEY_LEN)
 #endif
 
 #ifdef HAVE_GTK
@@ -4806,6 +4812,21 @@ cmd_disco(ProfWin* window, const char* const command, gchar** args)
     return TRUE;
 }
 
+char *create_aesgcm_fragment(unsigned char *key, int key_size,
+                             unsigned char *nonce, int nonce_size) {
+    char fragment[(nonce_size+key_size)*2+1];
+
+    for (int i = 0; i < nonce_size; i++) {
+        sprintf(&(fragment[i*2]), "%02x", nonce[i]);
+    }
+
+    for (int i = 0; i < key_size; i++) {
+        sprintf(&(fragment[(i+nonce_size)*2]), "%02x", key[i]);
+    }
+
+    return strdup(fragment);
+}
+
 gboolean
 cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
 {
@@ -4849,6 +4870,8 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
     }
 
     FILE *fh = fdopen(fd, "rb");
+    char *alt_scheme = NULL;
+    char *alt_fragment = NULL;
 
     switch (window->type) {
         case WIN_MUC:
@@ -4898,12 +4921,17 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
                 fflush(tmpfh);
                 rewind(tmpfh);
 
-                fclose(fh);
+                fclose(fh); // Also closes descriptor.
 
                 // Switch original stream with temporary encrypted stream.
                 fd = tmpfd;
                 fh = tmpfh;
 
+                alt_scheme = AESGCM_URL_SCHEME;
+                alt_fragment = create_aesgcm_fragment(
+                        key, AES256_GCM_KEY_LENGTH,
+                        nonce, AES256_GCM_NONCE_LENGTH);
+
                 break;
             }
 
@@ -4944,6 +4972,8 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
     upload->filehandle = fh;
     upload->filesize = file_size(fd);
     upload->mime_type = file_mime_type(filename);
+    upload->alt_scheme = alt_scheme;
+    upload->alt_fragment = alt_fragment;
 
     iq_http_upload_request(upload);
 
diff --git a/src/tools/http_upload.c b/src/tools/http_upload.c
index 5f725851..69587c08 100644
--- a/src/tools/http_upload.c
+++ b/src/tools/http_upload.c
@@ -128,8 +128,35 @@ _data_callback(void* ptr, size_t size, size_t nmemb, void* data)
     return realsize;
 }
 
-void*
-http_file_put(void* userdata)
+int format_alt_url(char *original_url, char *new_scheme, char *new_fragment, char **new_url) {
+    int ret = 0;
+    CURLU *h = curl_url();
+
+    if ((ret = curl_url_set(h, CURLUPART_URL, original_url, 0)) != 0) {
+        goto out;
+    }
+
+    if (new_scheme != NULL) {
+        if ((ret = curl_url_set(h, CURLUPART_SCHEME, new_scheme, CURLU_NON_SUPPORT_SCHEME)) != 0) {
+            goto out;
+        }
+    }
+
+    if (new_fragment != NULL) {
+        if ((ret = curl_url_set(h, CURLUPART_FRAGMENT, new_fragment, 0)) != 0) {
+            goto out;
+        }
+    }
+
+    ret = curl_url_get(h, CURLUPART_URL, new_url, 0);
+
+out:
+    curl_url_cleanup(h);
+    return ret;
+}
+
+void *
+http_file_put(void *userdata)
 {
     HTTPUpload* upload = (HTTPUpload*)userdata;
 
@@ -256,30 +283,40 @@ http_file_put(void* userdata)
             win_mark_received(upload->window, upload->put_url);
             free(msg);
 
-            switch (upload->window->type) {
-            case WIN_CHAT:
-            {
-                ProfChatWin* chatwin = (ProfChatWin*)(upload->window);
-                assert(chatwin->memcheck == PROFCHATWIN_MEMCHECK);
-                cl_ev_send_msg(chatwin, upload->get_url, upload->get_url);
-                break;
-            }
-            case WIN_PRIVATE:
-            {
-                ProfPrivateWin* privatewin = (ProfPrivateWin*)(upload->window);
-                assert(privatewin->memcheck == PROFPRIVATEWIN_MEMCHECK);
-                cl_ev_send_priv_msg(privatewin, upload->get_url, upload->get_url);
-                break;
-            }
-            case WIN_MUC:
-            {
-                ProfMucWin* mucwin = (ProfMucWin*)(upload->window);
-                assert(mucwin->memcheck == PROFMUCWIN_MEMCHECK);
-                cl_ev_send_muc_msg(mucwin, upload->get_url, upload->get_url);
-                break;
-            }
-            default:
-                break;
+            char *url = NULL;
+            if (format_alt_url(upload->get_url, upload->alt_scheme, upload->alt_fragment, &url) != 0) {
+                char *msg;
+                asprintf(&msg, "Uploading '%s' failed: Bad URL ('%s')", upload->filename, upload->get_url);
+                cons_show_error(msg);
+                free(msg);
+            } else {
+                switch (upload->window->type) {
+                case WIN_CHAT:
+                {
+                    ProfChatWin *chatwin = (ProfChatWin*)(upload->window);
+                    assert(chatwin->memcheck == PROFCHATWIN_MEMCHECK);
+                    cl_ev_send_msg(chatwin, url, url);
+                    break;
+                }
+                case WIN_PRIVATE:
+                {
+                    ProfPrivateWin *privatewin = (ProfPrivateWin*)(upload->window);
+                    assert(privatewin->memcheck == PROFPRIVATEWIN_MEMCHECK);
+                    cl_ev_send_priv_msg(privatewin, url, url);
+                    break;
+                }
+                case WIN_MUC:
+                {
+                    ProfMucWin *mucwin = (ProfMucWin*)(upload->window);
+                    assert(mucwin->memcheck == PROFMUCWIN_MEMCHECK);
+                    cl_ev_send_muc_msg(mucwin, url, url);
+                    break;
+                }
+                default:
+                    break;
+                }
+
+                curl_free(url);
             }
         }
     }
diff --git a/src/tools/http_upload.h b/src/tools/http_upload.h
index 5b3b4754..9e801973 100644
--- a/src/tools/http_upload.h
+++ b/src/tools/http_upload.h
@@ -50,10 +50,12 @@ typedef struct http_upload_t {
     FILE *filehandle;
     off_t filesize;
     curl_off_t bytes_sent;
-    char* mime_type;
-    char* get_url;
-    char* put_url;
-    ProfWin* window;
+    char *mime_type;
+    char *get_url;
+    char *put_url;
+    char *alt_scheme;
+    char *alt_fragment;
+    ProfWin *window;
     pthread_t worker;
     int cancel;
 } HTTPUpload;