diff --git a/src/command/cmd_funcs.c b/src/command/cmd_funcs.c
index c37cc51b..23f0b98d 100644
--- a/src/command/cmd_funcs.c
+++ b/src/command/cmd_funcs.c
@@ -4811,7 +4811,6 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
 {
     jabber_conn_status_t conn_status = connection_get_status();
     char *filename = args[0];
-    char *filepath = NULL;
     unsigned char *key = NULL;
 
     // expand ~ to $HOME
@@ -4823,7 +4822,15 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
         filename = strdup(filename);
     }
 
-    filepath = strdup(filename);
+    if (access(filename, R_OK) != 0) {
+        cons_show_error("Uploading '%s' failed: File not found!", filename);
+        goto out;
+    }
+
+    if (!is_regular_file(filename)) {
+        cons_show_error("Uploading '%s' failed: Not a file!", filename);
+        goto out;
+    }
 
     if (conn_status != JABBER_CONNECTED) {
         cons_show("You are not currently connected.");
@@ -4835,6 +4842,14 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
         goto out;
     }
 
+    int fd;
+    if ((fd = open(filename, O_RDONLY)) == -1) {
+        cons_show_error("Unable to open file descriptor for '%s'.", filename);
+        goto out;
+    }
+
+    FILE *fh = fdopen(fd, "rb");
+
     switch (window->type) {
         case WIN_MUC:
         case WIN_CHAT:
@@ -4844,37 +4859,14 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
 
             if (chatwin->is_omemo && !prefs_get_boolean(PREF_OMEMO_SENDFILE)) {
                 int tmpfd;
-                GError *err = NULL;
-                char *tmppath = NULL;
-
-                tmpfd = g_file_open_tmp("profanity.XXXXXX", &tmppath, &err);
-                if (err != NULL) {
+                if ((tmpfd = g_file_open_tmp("profanity.XXXXXX", NULL, NULL)) == -1) {
                     cons_show_error("Unable to create temporary file for encrypted transfer.");
                     win_println(window, THEME_ERROR, "-", "Unable to create temporary file for encrypted transfer.");
+                    fclose(fh);
                     goto out;
                 }
 
-                struct stat tmpst;
-                if (fstat(tmpfd, &tmpst)) {
-                    cons_show_error("Cannot determine file size.");
-                    win_println(window, THEME_ERROR, "-", "Cannot determine file size.");
-                    goto out;
-                }
-
-                FILE *tmpfile = fdopen(tmpfd, "wb");
-                if (tmpfile == NULL) {
-                    cons_show_error("Unable to open temporary file.");
-                    win_println(window, THEME_ERROR, "-", "Unable to open temporary file.");
-                    goto out;
-                }
-
-                FILE *infile = fopen(filepath, "rb");
-                if (infile == NULL) {
-                    cons_show_error("Unable to open file.");
-                    win_println(window, THEME_ERROR, "-", "Unable to open file.");
-                    close(tmpfd);
-                    goto out;
-                }
+                FILE *tmpfh = fdopen(tmpfd, "wb");
 
                 int crypt_res = GPG_ERR_NO_ERROR;
 
@@ -4884,22 +4876,33 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
                 if (key == NULL) {
                     cons_show_error("Cannot allocate secure memory for encryption.");
                     win_println(window, THEME_ERROR, "-", "Cannot allocate secure memory for encryption.");
+                    fclose(fh);
+                    fclose(tmpfh);
                     goto out;
                 }
 
                 key = gcry_random_bytes_secure(AES256_GCM_KEY_LENGTH, GCRY_VERY_STRONG_RANDOM);
                 gcry_create_nonce(nonce, AES256_GCM_NONCE_LENGTH);
 
-                crypt_res = aes256gcm_encrypt_file(infile, tmpfile, tmpst.st_size, key, nonce);
+                crypt_res = aes256gcm_encrypt_file(fh, tmpfh, file_size(fd), key, nonce);
 
                 if (crypt_res != 0) {
                     cons_show_error("Failed to encrypt file.");
                     win_println(window, THEME_ERROR, "-", "Failed to encrypt file.");
+                    fclose(fh);
+                    fclose(tmpfh);
                     goto out;
                 }
 
-                free(filepath);
-                filepath = tmppath;
+                // Force flush as the upload will read from the same stream.
+                fflush(tmpfh);
+                rewind(tmpfh);
+
+                fclose(fh);
+
+                // Switch original stream with temporary encrypted stream.
+                fd = tmpfd;
+                fh = tmpfh;
 
                 break;
             }
@@ -4934,21 +4937,12 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
         return TRUE;
     }
 
-    if (access(filename, R_OK) != 0) {
-        cons_show_error("Uploading '%s' failed: File not found!", filename);
-        goto out;
-    }
-
-    if (!is_regular_file(filename)) {
-        cons_show_error("Uploading '%s' failed: Not a file!", filename);
-        goto out;
-    }
-
-    HTTPUpload* upload = malloc(sizeof(HTTPUpload));
+    HTTPUpload *upload = malloc(sizeof(HTTPUpload));
     upload->window = window;
 
-    upload->filename = filename;
-    upload->filesize = file_size(filename);
+    upload->filename = strdup(filename);
+    upload->filehandle = fh;
+    upload->filesize = file_size(fd);
     upload->mime_type = file_mime_type(filename);
 
     iq_http_upload_request(upload);
@@ -4958,8 +4952,6 @@ out:
         gcry_free(key);
     if (filename != NULL)
         free(filename);
-    if (filepath != NULL)
-        free(filepath);
 
     return TRUE;
 }
diff --git a/src/tools/http_upload.c b/src/tools/http_upload.c
index 68de57ed..5f725851 100644
--- a/src/tools/http_upload.c
+++ b/src/tools/http_upload.c
@@ -133,7 +133,7 @@ http_file_put(void* userdata)
 {
     HTTPUpload* upload = (HTTPUpload*)userdata;
 
-    FILE* fd = NULL;
+    FILE *fh = NULL;
 
     char* err = NULL;
     char* content_type_header;
@@ -146,7 +146,7 @@ http_file_put(void* userdata)
 
     pthread_mutex_lock(&lock);
     char* msg;
-    if (asprintf(&msg, "Uploading '%s': 0%%", upload->filepath) == -1) {
+    if (asprintf(&msg, "Uploading '%s': 0%%", upload->filename) == -1) {
         msg = strdup(FALLBACK_MSG);
     }
     win_print_http_upload(upload->window, msg, upload->put_url);
@@ -186,18 +186,13 @@ http_file_put(void* userdata)
 
     curl_easy_setopt(curl, CURLOPT_USERAGENT, "profanity");
 
-    if (!(fd = fopen(upload->filepath, "rb"))) {
-        if (asprintf(&err, "failed to open '%s'", upload->filepath) == -1) {
-            err = NULL;
-        }
-        goto end;
-    }
+    fh = upload->filehandle;
 
     if (cert_path) {
         curl_easy_setopt(curl, CURLOPT_CAPATH, cert_path);
     }
 
-    curl_easy_setopt(curl, CURLOPT_READDATA, fd);
+    curl_easy_setopt(curl, CURLOPT_READDATA, fh);
     curl_easy_setopt(curl, CURLOPT_INFILESIZE_LARGE, (curl_off_t)(upload->filesize));
     curl_easy_setopt(curl, CURLOPT_UPLOAD, 1L);
 
@@ -225,12 +220,11 @@ http_file_put(void* userdata)
 #endif
     }
 
-end:
     curl_easy_cleanup(curl);
     curl_global_cleanup();
     curl_slist_free_all(headers);
-    if (fd) {
-        fclose(fd);
+    if (fh) {
+        fclose(fh);
     }
     free(content_type_header);
     free(output.buffer);
@@ -294,7 +288,6 @@ end:
     pthread_mutex_unlock(&lock);
 
     free(upload->filename);
-    free(upload->filepath);
     free(upload->mime_type);
     free(upload->get_url);
     free(upload->put_url);
@@ -304,18 +297,18 @@ end:
 }
 
 char*
-file_mime_type(const char* const filepath)
+file_mime_type(const char* const filename)
 {
     char* out_mime_type;
     char file_header[FILE_HEADER_BYTES];
-    FILE *fd;
-    if (!(fd = fopen(filepath, "rb"))) {
+    FILE *fh;
+    if (!(fh = fopen(filename, "rb"))) {
         return strdup(FALLBACK_MIMETYPE);
     }
-    size_t file_header_size = fread(file_header, 1, FILE_HEADER_BYTES, fd);
-    fclose(fd);
+    size_t file_header_size = fread(file_header, 1, FILE_HEADER_BYTES, fh);
+    fclose(fh);
 
-    char *content_type = g_content_type_guess(filepath, (unsigned char*)file_header, file_header_size, NULL);
+    char *content_type = g_content_type_guess(filename, (unsigned char*)file_header, file_header_size, NULL);
     if (content_type != NULL) {
         char* mime_type = g_content_type_get_mime_type(content_type);
         out_mime_type = strdup(mime_type);
@@ -327,10 +320,10 @@ file_mime_type(const char* const filepath)
     return out_mime_type;
 }
 
-off_t file_size(const char* const filepath)
+off_t file_size(int filedes)
 {
     struct stat st;
-    stat(filepath, &st);
+    fstat(filedes, &st);
     return st.st_size;
 }
 
diff --git a/src/tools/http_upload.h b/src/tools/http_upload.h
index cbab96ed..5b3b4754 100644
--- a/src/tools/http_upload.h
+++ b/src/tools/http_upload.h
@@ -47,7 +47,7 @@
 
 typedef struct http_upload_t {
     char *filename;
-    char *filepath;
+    FILE *filehandle;
     off_t filesize;
     curl_off_t bytes_sent;
     char* mime_type;
@@ -60,8 +60,8 @@ typedef struct http_upload_t {
 
 void* http_file_put(void* userdata);
 
-char* file_mime_type(const char* const filepath);
-off_t file_size(const char* const filepath);
+char* file_mime_type(const char* const filename);
+off_t file_size(int filedes);
 
 void http_upload_cancel_processes(ProfWin* window);
 void http_upload_add_upload(HTTPUpload* upload);
diff --git a/src/xmpp/iq.c b/src/xmpp/iq.c
index 1c7d16e7..07acdf14 100644
--- a/src/xmpp/iq.c
+++ b/src/xmpp/iq.c
@@ -2401,9 +2401,9 @@ _http_upload_response_id_handler(xmpp_stanza_t* const stanza, void* const userda
     if (g_strcmp0(type, STANZA_TYPE_ERROR) == 0) {
         char* error_message = stanza_get_error_message(stanza);
         if (from) {
-            cons_show_error("Uploading '%s' failed for %s: %s", upload->filepath, from, error_message);
+            cons_show_error("Uploading '%s' failed for %s: %s", upload->filename, from, error_message);
         } else {
-            cons_show_error("Uploading '%s' failed: %s", upload->filepath, error_message);
+            cons_show_error("Uploading '%s' failed: %s", upload->filename, error_message);
         }
         free(error_message);
         return 0;