diff --git a/pixstrip-cli/src/main.rs b/pixstrip-cli/src/main.rs
index 7759516..6217e10 100644
--- a/pixstrip-cli/src/main.rs
+++ b/pixstrip-cli/src/main.rs
@@ -535,13 +535,15 @@ fn cmd_undo(count: usize) {
             let undo_count = count.min(entries.len());
             let to_undo = entries.split_off(entries.len() - undo_count);
             let mut total_trashed = 0;
+            let mut failed_entries = Vec::new();
 
-            for entry in &to_undo {
+            for entry in to_undo {
                 if entry.output_files.is_empty() {
                     println!(
                         "Batch from {} has no recorded output files - cannot undo",
                         entry.timestamp
                     );
+                    failed_entries.push(entry);
                     continue;
                 }
 
@@ -550,11 +552,13 @@ fn cmd_undo(count: usize) {
                     entry.total, entry.input_dir
                 );
 
+                let mut batch_trashed = 0;
                 for file_path in &entry.output_files {
                     let path = PathBuf::from(file_path);
                     if path.exists() {
                         match trash::delete(&path) {
                             Ok(()) => {
+                                batch_trashed += 1;
                                 total_trashed += 1;
                             }
                             Err(e) => {
@@ -563,9 +567,17 @@ fn cmd_undo(count: usize) {
                         }
                     }
                 }
+
+                // Keep entry in history if no files were trashed
+                if batch_trashed == 0 {
+                    failed_entries.push(entry);
+                }
             }
 
-            // Remove undone entries from history
+            // Re-add entries where trash failed so they can be retried
+            entries.extend(failed_entries);
+
+            // Write updated history
             if let Err(e) = history.write_all(&entries) {
                 eprintln!("Warning: failed to update history after undo: {}", e);
             }
@@ -706,8 +718,17 @@ fn cmd_watch_remove(path: &str) {
         return;
     }
 
-    if let Ok(json) = serde_json::to_string_pretty(&watches) {
-        let _ = std::fs::write(&watches_path, json);
+    match serde_json::to_string_pretty(&watches) {
+        Ok(json) => {
+            if let Err(e) = std::fs::write(&watches_path, json) {
+                eprintln!("Failed to write watch config: {}", e);
+                std::process::exit(1);
+            }
+        }
+        Err(e) => {
+            eprintln!("Failed to serialize watch config: {}", e);
+            std::process::exit(1);
+        }
     }
     println!("Removed watch folder: {}", path);
 }
diff --git a/pixstrip-core/src/executor.rs b/pixstrip-core/src/executor.rs
index b4c2a31..c4f1566 100644
--- a/pixstrip-core/src/executor.rs
+++ b/pixstrip-core/src/executor.rs
@@ -723,10 +723,11 @@ fn paths_are_same(a: &std::path::Path, b: &std::path::Path) -> bool {
     }
 }
 
-/// Remove a 0-byte placeholder file created by find_unique_path on error.
+/// Remove a placeholder file created by find_unique_path on error.
+/// Placeholders are either 0-byte (no marker) or 1-byte (marker `~`).
 fn cleanup_placeholder(path: &std::path::Path) {
     if let Ok(meta) = std::fs::metadata(path) {
-        if meta.len() == 0 {
+        if meta.len() <= 1 {
             let _ = std::fs::remove_file(path);
         }
     }
diff --git a/pixstrip-core/src/operations/rename.rs b/pixstrip-core/src/operations/rename.rs
index b2ac266..56c20bb 100644
--- a/pixstrip-core/src/operations/rename.rs
+++ b/pixstrip-core/src/operations/rename.rs
@@ -40,9 +40,15 @@ pub fn apply_template_full(
         result = result.replace("{counter}", &counter.to_string());
     }
 
-    if let Some((w, h)) = dimensions {
-        result = result.replace("{width}", &w.to_string());
-        result = result.replace("{height}", &h.to_string());
+    match dimensions {
+        Some((w, h)) => {
+            result = result.replace("{width}", &w.to_string());
+            result = result.replace("{height}", &h.to_string());
+        }
+        None => {
+            result = result.replace("{width}", "0");
+            result = result.replace("{height}", "0");
+        }
     }
 
     // {date} - today's date
diff --git a/pixstrip-core/src/operations/watermark.rs b/pixstrip-core/src/operations/watermark.rs
index 0595d59..a74162d 100644
--- a/pixstrip-core/src/operations/watermark.rs
+++ b/pixstrip-core/src/operations/watermark.rs
@@ -168,7 +168,7 @@ fn render_text_to_image(
     opacity: f32,
 ) -> image::RgbaImage {
     let scale = ab_glyph::PxScale::from(font_size);
-    let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 0.6) as u32).saturating_add(4).min(8192);
+    let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 1.0) as u32).saturating_add(4).min(16384);
     let text_height = ((font_size.min(1000.0) * 1.4) as u32).saturating_add(4).min(4096);
 
     let alpha = (opacity * 255.0).clamp(0.0, 255.0) as u8;
@@ -266,7 +266,7 @@ fn apply_text_watermark(
     } else {
         // No rotation - draw text directly (faster)
         let scale = ab_glyph::PxScale::from(font_size);
-        let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 0.6) as u32).saturating_add(4).min(8192);
+        let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 1.0) as u32).saturating_add(4).min(16384);
         let text_height = ((font_size.min(1000.0) * 1.4) as u32).saturating_add(4).min(4096);
         let text_dims = Dimensions {
             width: text_width,
@@ -336,7 +336,7 @@ fn apply_tiled_text_watermark(
         let alpha = (opacity * 255.0).clamp(0.0, 255.0) as u8;
         let draw_color = Rgba([color[0], color[1], color[2], alpha]);
 
-        let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 0.6) as i64 + 4).min(8192);
+        let text_width = ((text.chars().count().min(10_000) as f32 * font_size.min(1000.0) * 1.0) as i64 + 4).min(16384);
         let text_height = ((font_size.min(1000.0) * 1.4) as i64 + 4).min(4096);
 
         let mut y = spacing as i64;