diff --git a/src/app.rs b/src/app.rs
index 254827b..0561db4 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -422,6 +422,7 @@ pub enum Message {
     CheckClipboardImage,
     CheckClipboardVideo,
     CheckClipboardText,
+    RetryCheckClipboard(ClipboardCache),
     ClipboardCached(ClipboardCache),
     PendingCancel(u64),
     PendingCancelAll,
@@ -4036,9 +4037,12 @@ impl Application for App {
                 // Check if clipboard has any paste-able content and cache it
                 return clipboard::read_data::<ClipboardPaste>().map(|contents_opt| {
                     match contents_opt {
-                        Some(contents) if !contents.paths.is_empty() => cosmic::action::app(
-                            Message::ClipboardCached(ClipboardCache::Files(contents)),
+                        Some(contents) if contents.paths.is_empty() => cosmic::action::app(
+                            Message::RetryCheckClipboard(ClipboardCache::Files(contents)),
                         ),
+                        Some(contents) => cosmic::action::app(Message::ClipboardCached(
+                            ClipboardCache::Files(contents),
+                        )),
                         _ => cosmic::action::app(Message::CheckClipboardImage),
                     }
                 });
@@ -4071,6 +4075,28 @@ impl Application for App {
                     }))
                 });
             }
+            Message::RetryCheckClipboard(cache) => {
+                let mut cmds = Vec::new();
+                cmds.push(self.update(Message::ClipboardCached(cache)));
+
+                cmds.push(
+                    iced::Task::future(tokio::time::sleep(Duration::from_millis(300)))
+                        .discard()
+                        .chain(
+                            clipboard::read_data::<ClipboardPaste>().map(|contents_opt| {
+                                match contents_opt {
+                                    Some(contents) if !contents.paths.is_empty() => {
+                                        cosmic::action::app(Message::ClipboardCached(
+                                            ClipboardCache::Files(contents),
+                                        ))
+                                    }
+                                    _ => cosmic::action::app(Message::CheckClipboardImage),
+                                }
+                            }),
+                        ),
+                );
+                return Task::batch(cmds);
+            }
             Message::ClipboardCached(cache) => {
                 self.clipboard_cache = cache;
             }
@@ -4478,6 +4504,7 @@ impl Application for App {
                                             widget::Id::unique(),
                                         )),
                                     );
+                                    commands.push(self.update(Message::CheckClipboard));
                                     commands.push(self.update(Message::Surface(
                                         cosmic::surface::action::app_popup(
                                             move |app: &mut Self| -> SctkPopupSettings {
@@ -5344,7 +5371,11 @@ impl Application for App {
                     };
                 }
                 // Check clipboard when window gains focus
-                return self.update(Message::CheckClipboard);
+                // HACK: Wait a moment for the data to be available.
+                return cosmic::task::future(async {
+                    _ = tokio::time::sleep(Duration::from_millis(300)).await;
+                    cosmic::action::app(Message::CheckClipboard)
+                });
             }
             Message::Surface(action) => {
                 return cosmic::task::message(cosmic::Action::Cosmic(
diff --git a/src/clipboard.rs b/src/clipboard.rs
index 6b0be96..5892071 100644
--- a/src/clipboard.rs
+++ b/src/clipboard.rs
@@ -133,9 +133,7 @@ impl TryFrom<(Vec<u8>, String)> for ClipboardPaste {
             "text/uri-list" => {
                 let text = str::from_utf8(&data)?;
                 let lines = text.lines();
-                if text.is_empty() || lines.count() == 0 {
-                    Err(format!("Empty file url"))?;
-                }
+
                 for line in text.lines() {
                     let url = Url::parse(line)?;
                     match url.to_file_path() {
@@ -146,10 +144,7 @@ impl TryFrom<(Vec<u8>, String)> for ClipboardPaste {
             }
             "x-special/gnome-copied-files" => {
                 let text = str::from_utf8(&data)?;
-                let lines = text.lines();
-                if text.is_empty() || lines.count() == 0 {
-                    Err(format!("Empty file url"))?;
-                }
+
                 for (i, line) in text.lines().enumerate() {
                     if i == 0 {
                         kind = match line {