diff --git a/src/command/cmd_funcs.c b/src/command/cmd_funcs.c
index dbf92d21..68d6188a 100644
--- a/src/command/cmd_funcs.c
+++ b/src/command/cmd_funcs.c
@@ -9209,18 +9209,30 @@ _prepare_filename(ProfWin* window, gchar* url, gchar* path)
         break;
     }
 
-    // Ensure that the downloads directory exists for saving cleartexts.
-    auto_gchar gchar* downloads_dir = path ? get_expanded_path(path) : files_get_download_path(jid);
-    if (g_mkdir_with_parents(downloads_dir, S_IRWXU) != 0) {
-        cons_show_error("Failed to create download directory "
-                        "at '%s' with error '%s'",
-                        downloads_dir, strerror(errno));
-        return NULL;
+    auto_gchar gchar* expanded_path = path ? get_expanded_path(path) : files_get_download_path(jid);
+
+    // If path is provided and doesn't look like a directory, create its parent.
+    // Otherwise, create the directory itself.
+    if (path && !g_str_has_suffix(expanded_path, G_DIR_SEPARATOR_S) && !g_file_test(expanded_path, G_FILE_TEST_IS_DIR)) {
+        auto_gchar gchar* dirname = g_path_get_dirname(expanded_path);
+        if (g_mkdir_with_parents(dirname, S_IRWXU) != 0) {
+            cons_show_error("Failed to create download directory "
+                            "at '%s' with error '%s'",
+                            dirname, strerror(errno));
+            return NULL;
+        }
+    } else {
+        if (g_mkdir_with_parents(expanded_path, S_IRWXU) != 0) {
+            cons_show_error("Failed to create download directory "
+                            "at '%s' with error '%s'",
+                            expanded_path, strerror(errno));
+            return NULL;
+        }
     }
 
     // Generate an unique filename from the URL that should be stored in the
     // downloads directory.
-    return unique_filename_from_url(url, downloads_dir);
+    return unique_filename_from_url(url, expanded_path);
 }
 
 #ifdef HAVE_OMEMO
diff --git a/src/tools/aesgcm_download.c b/src/tools/aesgcm_download.c
index 1c34074e..b7e7cd85 100644
--- a/src/tools/aesgcm_download.c
+++ b/src/tools/aesgcm_download.c
@@ -43,7 +43,7 @@ aesgcm_file_get(void* userdata)
     // and tag stored in the URL fragment.
     if (omemo_parse_aesgcm_url(aesgcm_dl->url, &https_url, &fragment) != 0) {
         cons_show_error("Download failed: Cannot parse URL '%s'.", aesgcm_dl->url);
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                    "Download failed: Cannot parse URL '%s'.",
                                    aesgcm_dl->url);
         return NULL;
@@ -54,7 +54,7 @@ aesgcm_file_get(void* userdata)
     auto_gchar gchar* tmpname = NULL;
     auto_gfd gint tmpfd = 0;
     if ((tmpfd = g_file_open_tmp("profanity.XXXXXX", &tmpname, NULL)) == -1) {
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                    "Downloading '%s' failed: Unable to create "
                                    "temporary ciphertext file for writing "
                                    "(%s).",
@@ -65,7 +65,7 @@ aesgcm_file_get(void* userdata)
     // Open the target file for storing the cleartext.
     auto_FILE FILE* outfh = fopen(aesgcm_dl->filename, "wb");
     if (outfh == NULL) {
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                    "Downloading '%s' failed: Unable to open "
                                    "output file at '%s' for writing (%s).",
                                    https_url, aesgcm_dl->filename,
@@ -80,9 +80,11 @@ aesgcm_file_get(void* userdata)
     http_dl->worker = aesgcm_dl->worker;
     http_dl->id = strdup(aesgcm_dl->id);
     http_dl->url = strdup(https_url);
+    http_dl->display_url = strdup(aesgcm_dl->url);
     http_dl->filename = strdup(tmpname);
     http_dl->cmd_template = NULL;
     http_dl->silent = FALSE;
+    http_dl->silent_done = TRUE;
     http_dl->return_bytes_received = TRUE;
     aesgcm_dl->http_dl = http_dl;
 
@@ -95,7 +97,7 @@ aesgcm_file_get(void* userdata)
 
     FILE* tmpfh = fopen(tmpname, "rb");
     if (tmpfh == NULL) {
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                    "Downloading '%s' failed: Unable to open "
                                    "temporary file at '%s' for reading (%s).",
                                    aesgcm_dl->url, tmpname,
@@ -110,13 +112,15 @@ aesgcm_file_get(void* userdata)
     remove(tmpname);
 
     if (crypt_res != GPG_ERR_NO_ERROR) {
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                    "Downloading '%s' failed: Failed to decrypt "
                                    "file (%s).",
-                                   https_url, gcry_strerror(crypt_res));
+                                   aesgcm_dl->url, gcry_strerror(crypt_res));
     } else {
-        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
-                                   "Decrypted file saved to '%s'", aesgcm_dl->filename);
+        http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ONLINE, ENTRY_COMPLETED,
+                                   "Downloading '%s': done\nSaved to '%s'",
+                                   aesgcm_dl->url, aesgcm_dl->filename);
+        win_mark_received(aesgcm_dl->window, aesgcm_dl->id);
     }
 
     if (aesgcm_dl->cmd_template != NULL) {
@@ -126,7 +130,7 @@ aesgcm_file_get(void* userdata)
 
         // TODO: Log the error.
         if (!call_external(argv)) {
-            http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
+            http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id, THEME_ERROR, ENTRY_ERROR,
                                        "Downloading '%s' failed: Unable to call "
                                        "command '%s' with file at '%s' (%s).",
                                        aesgcm_dl->url,
diff --git a/src/tools/http_common.c b/src/tools/http_common.c
index cfec1bcf..0386e08d 100644
--- a/src/tools/http_common.c
+++ b/src/tools/http_common.c
@@ -19,7 +19,7 @@
 #define FALLBACK_MSG ""
 
 void
-http_print_transfer_update(ProfWin* window, char* id, const char* fmt, ...)
+http_print_transfer_update(ProfWin* window, char* id, theme_item_t theme_item, int flags, const char* fmt, ...)
 {
     va_list args;
 
@@ -29,7 +29,7 @@ http_print_transfer_update(ProfWin* window, char* id, const char* fmt, ...)
     va_end(args);
 
     if (window->type != WIN_CONSOLE) {
-        win_update_entry_message(window, id, msg->str);
+        win_update_entry(window, id, msg->str, theme_item, flags);
     } else {
         cons_show("%s", msg->str);
     }
@@ -38,7 +38,7 @@ http_print_transfer_update(ProfWin* window, char* id, const char* fmt, ...)
 }
 
 void
-http_print_transfer(ProfWin* window, char* id, const char* fmt, ...)
+http_print_transfer(ProfWin* window, char* id, theme_item_t theme_item, const char* fmt, ...)
 {
     va_list args;
 
@@ -47,7 +47,7 @@ http_print_transfer(ProfWin* window, char* id, const char* fmt, ...)
     g_string_vprintf(msg, fmt, args);
     va_end(args);
 
-    win_print_http_transfer(window, msg->str, id);
+    win_print_status_with_id(window, msg->str, id, theme_item, 0);
 
     g_string_free(msg, TRUE);
 }
diff --git a/src/tools/http_common.h b/src/tools/http_common.h
index 529c05c9..f1f9b56a 100644
--- a/src/tools/http_common.h
+++ b/src/tools/http_common.h
@@ -12,7 +12,7 @@
 
 #include "ui/window.h"
 
-void http_print_transfer(ProfWin* window, char* id, const char* fmt, ...);
-void http_print_transfer_update(ProfWin* window, char* id, const char* fmt, ...);
+void http_print_transfer(ProfWin* window, char* id, theme_item_t theme_item, const char* fmt, ...);
+void http_print_transfer_update(ProfWin* window, char* id, theme_item_t theme_item, int flags, const char* fmt, ...);
 
 #endif
diff --git a/src/tools/http_download.c b/src/tools/http_download.c
index 720cc40c..bc561233 100644
--- a/src/tools/http_download.c
+++ b/src/tools/http_download.c
@@ -32,7 +32,6 @@
 #include "common.h"
 
 GSList* download_processes = NULL;
-gboolean silent = FALSE;
 
 static int
 _xferinfo(void* userdata, curl_off_t dltotal, curl_off_t dlnow, curl_off_t ultotal, curl_off_t ulnow)
@@ -58,9 +57,18 @@ _xferinfo(void* userdata, curl_off_t dltotal, curl_off_t dlnow, curl_off_t ultot
         dlperc = (100 * dlnow) / dltotal;
     }
 
-    if (!silent)
-        http_print_transfer_update(download->window, download->url,
-                                   "Downloading '%s': %d%%", download->url, dlperc);
+    if (!download->silent) {
+        const char* url = download->display_url ? download->display_url : download->url;
+        if (dlnow == dltotal && dltotal > 0) {
+            if (!download->silent_done) {
+                http_print_transfer_update(download->window, download->id, THEME_ONLINE, ENTRY_COMPLETED,
+                                           "Downloading '%s': done", url);
+            }
+        } else {
+            http_print_transfer_update(download->window, download->id, THEME_DEFAULT, 0,
+                                       "Downloading '%s': %d%%", url, dlperc);
+        }
+    }
 
     pthread_mutex_unlock(&lock);
 
@@ -85,20 +93,20 @@ http_file_get(void* userdata)
 
     CURL* curl;
     CURLcode res;
-    silent = download->silent;
 
     download->cancel = 0;
     download->bytes_received = 0;
 
     pthread_mutex_lock(&lock);
-    if (!silent) {
-        http_print_transfer(download->window, download->id,
-                            "Downloading '%s': 0%%", download->url);
+    const char* display_url = download->display_url ? download->display_url : download->url;
+    if (!download->silent) {
+        http_print_transfer(download->window, download->id, THEME_DEFAULT,
+                            "Downloading '%s': 0%%", display_url);
     }
 
     FILE* outfh = fopen(download->filename, "wb");
     if (outfh == NULL) {
-        http_print_transfer_update(download->window, download->id,
+        http_print_transfer_update(download->window, download->id, THEME_ERROR, ENTRY_ERROR,
                                    "Downloading '%s' failed: Unable to open "
                                    "output file at '%s' for writing (%s).",
                                    download->url, download->filename,
@@ -169,22 +177,24 @@ http_file_get(void* userdata)
     g_free(cert_path);
     if (err) {
         if (download->cancel) {
-            http_print_transfer_update(download->window, download->id,
+            http_print_transfer_update(download->window, download->id, THEME_ERROR, ENTRY_ERROR,
                                        "Downloading '%s' failed: "
                                        "Download was canceled",
-                                       download->url);
+                                       display_url);
         } else {
-            http_print_transfer_update(download->window, download->id,
+            http_print_transfer_update(download->window, download->id, THEME_ERROR, ENTRY_ERROR,
                                        "Downloading '%s' failed: %s",
-                                       download->url, err);
+                                       display_url, err);
         }
         free(err);
     } else {
-        if (!download->cancel && !silent) {
-            http_print_transfer_update(download->window, download->id,
-                                       "Downloading '%s': done\nSaved to '%s'",
-                                       download->url, download->filename);
-            win_mark_received(download->window, download->id);
+        if (!download->cancel) {
+            if (!download->silent && !download->silent_done) {
+                http_print_transfer_update(download->window, download->id, THEME_ONLINE, ENTRY_COMPLETED,
+                                           "Downloading '%s': done\nSaved to '%s'",
+                                           display_url, download->filename);
+                win_mark_received(download->window, download->id);
+            }
             if (download->return_bytes_received) {
                 ret = malloc(sizeof(*ret));
                 if (ret) {
@@ -201,10 +211,10 @@ http_file_get(void* userdata)
 
         // TODO: Log the error.
         if (!call_external(argv)) {
-            http_print_transfer_update(download->window, download->id,
+            http_print_transfer_update(download->window, download->id, THEME_ERROR, ENTRY_ERROR,
                                        "Downloading '%s' failed: Unable to call "
                                        "command '%s' with file at '%s' (%s).",
-                                       download->url,
+                                       display_url,
                                        download->cmd_template,
                                        download->filename,
                                        "TODO: Log the error");
@@ -221,6 +231,7 @@ out:
 
     free(download->filename);
     free(download->url);
+    free(download->display_url);
     free(download->id);
     free(download);
 
diff --git a/src/tools/http_download.h b/src/tools/http_download.h
index 4b7a40e7..c020e864 100644
--- a/src/tools/http_download.h
+++ b/src/tools/http_download.h
@@ -25,6 +25,7 @@ typedef struct http_download_t
 {
     char* id;
     char* url;
+    char* display_url;
     char* filename;
     char* cmd_template;
     curl_off_t bytes_received;
@@ -32,6 +33,7 @@ typedef struct http_download_t
     pthread_t worker;
     int cancel;
     gboolean silent;
+    gboolean silent_done;
     gboolean return_bytes_received;
 } HTTPDownload;
 
diff --git a/src/tools/http_upload.c b/src/tools/http_upload.c
index 6162034f..3cd7cb33 100644
--- a/src/tools/http_upload.c
+++ b/src/tools/http_upload.c
@@ -65,11 +65,21 @@ _xferinfo(void* userdata, curl_off_t dltotal, curl_off_t dlnow, curl_off_t ultot
         ulperc = (100 * ulnow) / ultotal;
     }
 
-    gchar* msg = g_strdup_printf("Uploading '%s': %d%%", upload->filename, ulperc);
+    gchar* msg = NULL;
+    theme_item_t theme = THEME_DEFAULT;
+    int flags = 0;
+    if (ulnow == ultotal && ultotal > 0) {
+        msg = g_strdup_printf("Uploading '%s': done", upload->filename);
+        theme = THEME_ONLINE;
+        flags = ENTRY_COMPLETED;
+    } else {
+        msg = g_strdup_printf("Uploading '%s': %d%%", upload->filename, ulperc);
+    }
+
     if (!msg) {
         msg = g_strdup(FALLBACK_MSG);
     }
-    win_update_entry_message(upload->window, upload->put_url, msg);
+    win_update_entry(upload->window, upload->put_url, msg, theme, flags);
     g_free(msg);
 
     pthread_mutex_unlock(&lock);
@@ -150,7 +160,7 @@ http_file_put(void* userdata)
     if (!msg) {
         msg = g_strdup(FALLBACK_MSG);
     }
-    win_print_http_transfer(upload->window, msg, upload->put_url);
+    win_print_status_with_id(upload->window, msg, upload->put_url, THEME_DEFAULT, 0);
 
     auto_gchar gchar* cert_path = prefs_get_string(PREF_TLS_CERTPATH);
     auto_gchar gchar* cafile = cafile_get_name();
@@ -278,21 +288,22 @@ http_file_put(void* userdata)
             if (!err_msg) {
                 err_msg = g_strdup(FALLBACK_MSG);
             }
+            win_update_entry(upload->window, upload->put_url, err_msg, THEME_ERROR, ENTRY_ERROR);
         } else {
             err_msg = g_strdup_printf("Uploading '%s' failed: %s", upload->filename, err);
             if (!err_msg) {
                 err_msg = g_strdup(FALLBACK_MSG);
             }
-            win_update_entry_message(upload->window, upload->put_url, err_msg);
+            win_update_entry(upload->window, upload->put_url, err_msg, THEME_ERROR, ENTRY_ERROR);
         }
         cons_show_error(err_msg);
     } else {
         if (!upload->cancel) {
-            auto_gchar gchar* status_msg = g_strdup_printf("Uploading '%s': 100%%", upload->filename);
+            auto_gchar gchar* status_msg = g_strdup_printf("Uploading '%s': done", upload->filename);
             if (!status_msg) {
                 status_msg = g_strdup(FALLBACK_MSG);
             }
-            win_update_entry_message(upload->window, upload->put_url, status_msg);
+            win_update_entry(upload->window, upload->put_url, status_msg, THEME_ONLINE, ENTRY_COMPLETED);
             win_mark_received(upload->window, upload->put_url);
 
             char* url = NULL;
diff --git a/src/ui/ui.h b/src/ui/ui.h
index f47bb906..ea0777db 100644
--- a/src/ui/ui.h
+++ b/src/ui/ui.h
@@ -25,12 +25,14 @@
 #include "otr/otr.h"
 #endif
 
-#define NO_ME          1
-#define NO_DATE        2
-#define NO_EOL         4
-#define NO_COLOUR_FROM 8
-#define NO_COLOUR_DATE 16
-#define UNTRUSTED      32
+#define NO_ME           1
+#define NO_DATE         2
+#define NO_EOL          4
+#define NO_COLOUR_FROM  8
+#define NO_COLOUR_DATE  16
+#define UNTRUSTED       32
+#define ENTRY_COMPLETED 64
+#define ENTRY_ERROR     128
 
 // core UI
 void ui_init(void);
diff --git a/src/ui/window.c b/src/ui/window.c
index 218e252d..2ee55176 100644
--- a/src/ui/window.c
+++ b/src/ui/window.c
@@ -1659,7 +1659,7 @@ win_appendln_highlight(ProfWin* window, theme_item_t theme_item, const char* con
 void
 win_print_http_transfer(ProfWin* window, const char* const message, char* id)
 {
-    win_print_outgoing_with_receipt(window, "!", NULL, message, id, NULL);
+    win_print_status_with_id(window, message, id, THEME_DEFAULT, 0);
 }
 
 void
@@ -1708,6 +1708,33 @@ win_update_entry_message(ProfWin* window, const char* const id, const char* cons
     }
 }
 
+void
+win_update_entry(ProfWin* window, const char* const id, const char* const message, theme_item_t theme_item, int flags)
+{
+    if (window->type == WIN_CONSOLE)
+        return;
+    ProfBuffEntry* entry = buffer_get_entry_by_id(window->layout->buffer, id);
+    if (entry) {
+        if (message) {
+            free(entry->message);
+            entry->message = strdup(message);
+        }
+        entry->theme_item = theme_item;
+        entry->flags |= flags;
+        win_redraw(window);
+    }
+}
+
+void
+win_print_status_with_id(ProfWin* window, const char* const message, char* id, theme_item_t theme_item, int flags)
+{
+    GDateTime* time = g_date_time_new_now_local();
+    int y_start_pos = getcury(window->layout->win);
+    _win_print_internal(window, "!", 0, time, flags, theme_item, NULL, message, NULL);
+    buffer_append(window->layout->buffer, "!", 0, time, flags, theme_item, NULL, NULL, message, NULL, id, y_start_pos, getcury(window->layout->win));
+    g_date_time_unref(time);
+}
+
 void
 win_remove_entry_message(ProfWin* window, const char* const id)
 {
diff --git a/src/ui/window.h b/src/ui/window.h
index 08e3e8e3..55665511 100644
--- a/src/ui/window.h
+++ b/src/ui/window.h
@@ -56,6 +56,8 @@ void win_sub_print(WINDOW* win, char* msg, gboolean newline, gboolean wrap, int
 void win_sub_newline_lazy(WINDOW* win);
 void win_mark_received(ProfWin* window, const char* const id);
 void win_update_entry_message(ProfWin* window, const char* const id, const char* const message);
+void win_update_entry(ProfWin* window, const char* const id, const char* const message, theme_item_t theme_item, int flags);
+void win_print_status_with_id(ProfWin* window, const char* const message, char* id, theme_item_t theme_item, int flags);
 
 gboolean win_has_active_subwin(ProfWin* window);