diff --git a/cmd/sync.go b/cmd/sync.go
index b4b72ff..89cf788 100644
--- a/cmd/sync.go
+++ b/cmd/sync.go
@@ -408,8 +408,11 @@ type groupedEvent struct {
 
 // groupFilesByTopLevel collapses file entries into top-level directories
 // and root files. "cmd/sync.go" + "cmd/init.go" become one entry "cmd/" with count=2.
+// When a directory contains only one file, the full relative path is kept.
 func groupFilesByTopLevel(files []syncer.FileEntry) []groupedEvent {
 	dirMap := make(map[string]*groupedEvent)
+	// Track the original filename for single-file groups.
+	dirFirstFile := make(map[string]string)
 	var rootFiles []groupedEvent
 	var dirOrder []string
 
@@ -429,6 +432,7 @@ func groupFilesByTopLevel(files []syncer.FileEntry) []groupedEvent {
 				g.bytes += f.Bytes
 			} else {
 				dirMap[dir] = &groupedEvent{name: dir, count: 1, bytes: f.Bytes}
+				dirFirstFile[dir] = f.Name
 				dirOrder = append(dirOrder, dir)
 			}
 		}
@@ -436,7 +440,11 @@ func groupFilesByTopLevel(files []syncer.FileEntry) []groupedEvent {
 
 	var out []groupedEvent
 	for _, dir := range dirOrder {
-		out = append(out, *dirMap[dir])
+		g := *dirMap[dir]
+		if g.count == 1 {
+			g.name = dirFirstFile[dir]
+		}
+		out = append(out, g)
 	}
 	out = append(out, rootFiles...)
 	return out
diff --git a/internal/tui/dashboard.go b/internal/tui/dashboard.go
index 33b2efa..7baabb8 100644
--- a/internal/tui/dashboard.go
+++ b/internal/tui/dashboard.go
@@ -256,14 +256,14 @@ func (m DashboardModel) renderEvent(evt SyncEvent) string {
 	ts := dimStyle.Render(evt.Time.Format("15:04:05"))
 	switch evt.Status {
 	case "synced":
-		name := padRight(evt.File, 30)
+		name := padRight(abbreviatePath(evt.File, 30), 30)
 		detail := ""
 		if evt.Size != "" {
 			detail = dimStyle.Render(fmt.Sprintf("%18s  %s", evt.Size, evt.Duration.Truncate(100*time.Millisecond)))
 		}
 		return ts + "  " + statusSynced.Render("✓") + " " + name + detail
 	case "error":
-		name := padRight(evt.File, 30)
+		name := padRight(abbreviatePath(evt.File, 30), 30)
 		return ts + "  " + statusError.Render("✗") + " " + name + statusError.Render("error")
 	default:
 		return ts + "  " + evt.File
@@ -285,6 +285,29 @@ func (m DashboardModel) filteredEvents() []SyncEvent {
 	return out
 }
 
+// abbreviatePath shortens a file path to fit within maxLen by replacing
+// leading directory segments with their first letter.
+// "internal/syncer/syncer.go" → "i/s/syncer.go"
+func abbreviatePath(p string, maxLen int) string {
+	if len(p) <= maxLen {
+		return p
+	}
+	parts := strings.Split(p, "/")
+	if len(parts) <= 1 {
+		return p
+	}
+	// Shorten directory segments from the left, keep the filename intact.
+	for i := 0; i < len(parts)-1; i++ {
+		if len(parts[i]) > 1 {
+			parts[i] = parts[i][:1]
+		}
+		if len(strings.Join(parts, "/")) <= maxLen {
+			break
+		}
+	}
+	return strings.Join(parts, "/")
+}
+
 // padRight pads s with spaces to width n, truncating if necessary.
 func padRight(s string, n int) string {
 	if len(s) >= n {