diff --git a/.jules/palette.md b/.jules/palette.md
index e048c06..564205e 100644
--- a/.jules/palette.md
+++ b/.jules/palette.md
@@ -9,3 +9,7 @@
 ## 2024-05-24 - Empty States in Process Lists
 **Learning:** Users can misinterpret an empty dynamic list (like processes) as a broken UI or a frozen app if there's no visual feedback indicating that the list is intentionally empty.
 **Action:** Always provide a clear, empty state with an icon and brief text for dynamic lists that might temporarily yield no results, preventing user confusion.
+
+## 2024-05-25 - Dynamic Button Labels and Contextual Disabled Help
+**Learning:** In async operations or disabled button states, static text like "Clean Selected" leaves the user guessing why a button is disabled (e.g. no selection) or if an action is currently running.
+**Action:** Use conditional labels (e.g., `viewModel.isScanning ? "Scanning..." : "Scan"`) and add `.help()` tooltips explaining exactly why a button is disabled (e.g. "Select items to clean") to provide immediate, clear feedback.
diff --git a/Sources/Cacheout/Views/ContentView.swift b/Sources/Cacheout/Views/ContentView.swift
index e242eac..f412971 100644
--- a/Sources/Cacheout/Views/ContentView.swift
+++ b/Sources/Cacheout/Views/ContentView.swift
@@ -222,19 +222,21 @@ struct ContentView: View {
                 Button {
                     Task { await viewModel.scan() }
                 } label: {
-                    Label("Scan", systemImage: "arrow.clockwise")
+                    Label(viewModel.isScanning ? "Scanning..." : "Scan", systemImage: "arrow.clockwise")
                 }
                 .disabled(viewModel.isScanning)
+                .help(viewModel.isScanning ? "Scan in progress" : "Scan for caches")
 
                 // Clean button
                 Button {
                     viewModel.showCleanConfirmation = true
                 } label: {
-                    Label("Clean Selected", systemImage: "trash")
+                    Label(viewModel.isCleaning ? "Cleaning..." : "Clean Selected", systemImage: "trash")
                 }
                 .buttonStyle(.borderedProminent)
                 .tint(.red)
                 .disabled(!viewModel.hasSelection || viewModel.isCleaning)
+                .help(!viewModel.hasSelection ? "Select items to clean" : (viewModel.isCleaning ? "Cleaning in progress" : "Clean selected items"))
             }
             .padding(.horizontal)
             .padding(.vertical, 10)