diff --git a/dots/.config/quickshell/ii/modules/ii/dock/DockAppButton.qml b/dots/.config/quickshell/ii/modules/ii/dock/DockAppButton.qml
index 8d2d270ae..bf199b0ae 100644
--- a/dots/.config/quickshell/ii/modules/ii/dock/DockAppButton.qml
+++ b/dots/.config/quickshell/ii/modules/ii/dock/DockAppButton.qml
@@ -18,7 +18,20 @@ DockButton {
     property bool appIsActive: appToplevel.toplevels.find(t => (t.activated == true)) !== undefined
 
     readonly property bool isSeparator: appToplevel.appId === "SEPARATOR"
-    readonly property var desktopEntry: DesktopEntries.heuristicLookup(appToplevel.appId)
+    property var desktopEntry: DesktopEntries.heuristicLookup(appToplevel.appId)
+
+    Timer {
+        // Retry looking up the desktop entry if it failed (e.g. database not loaded yet)
+        property int retryCount: 5
+        interval: 1000
+        running: !root.isSeparator && root.desktopEntry === null && retryCount > 0
+        repeat: true
+        onTriggered: {
+            retryCount--;
+            root.desktopEntry = DesktopEntries.heuristicLookup(root.appToplevel.appId);
+        }
+    }
+
     enabled: !isSeparator
     implicitWidth: isSeparator ? 1 : implicitHeight - topInset - bottomInset
 
diff --git a/dots/.config/quickshell/ii/modules/waffle/bar/tasks/TaskAppButton.qml b/dots/.config/quickshell/ii/modules/waffle/bar/tasks/TaskAppButton.qml
index 51e6b61a1..d4d7c072b 100644
--- a/dots/.config/quickshell/ii/modules/waffle/bar/tasks/TaskAppButton.qml
+++ b/dots/.config/quickshell/ii/modules/waffle/bar/tasks/TaskAppButton.qml
@@ -12,7 +12,20 @@ AppButton {
 
     required property var appEntry
     readonly property bool isSeparator: appEntry.appId === "SEPARATOR"
-    readonly property var desktopEntry: DesktopEntries.heuristicLookup(appEntry.appId)
+    property var desktopEntry: DesktopEntries.heuristicLookup(appEntry.appId)
+
+    Timer {
+        // Retry looking up the desktop entry if it failed (e.g. database not loaded yet)
+        property int retryCount: 5
+        interval: 1000
+        running: !root.isSeparator && root.desktopEntry === null && retryCount > 0
+        repeat: true
+        onTriggered: {
+            retryCount--;
+            root.desktopEntry = DesktopEntries.heuristicLookup(root.appEntry.appId);
+        }
+    }
+
     property bool active: root.appEntry.toplevels.some(t => t.activated)
     property bool hasWindows: appEntry.toplevels.length > 0