diff --git a/src/file/file_merge.sh b/src/file/file_merge.sh
index 7bc4d0a..97075d7 100644
--- a/src/file/file_merge.sh
+++ b/src/file/file_merge.sh
@@ -5,9 +5,9 @@ merge_files() {
   if [ "$strategy" == tree ]; then
     log info "[merge_files] Merging with $strategy strategy"
     if ! file_scan_tree "$base_files"; then
-      file_merge_tree "$base_files"
-      log info "[merge_files] Recursing"
-      merge_files "$base_files"
+      if ! file_merge_tree "$base_files"; then
+        merge_files "$base_files"
+      fi
     fi
   fi
 }
@@ -19,14 +19,13 @@ file_scan_tree() {
     local absolute_path="$(echo "$file" | sed 's/^base//')"
     local config_path="$CONFIG_ROOT/$file"
 
-    if ! diff "$absolute_path" "$config_path" > /dev/null; then
+    if ! diff "$absolute_path" "$config_path" > /dev/null 2>&1; then
       return 1
     fi
   done
   return 0
 }
 
-# TODO Check if files exist before acting
 file_merge_tree() {
   local base_files="$1"
   local strategy=
@@ -38,21 +37,32 @@ file_merge_tree() {
     local config_path="$CONFIG_ROOT/$file"
     log debug "[merge_tree] Config path: $config_path"
 
-    if diff "$absolute_path" "$config_path" > /dev/null; then
+    if diff "$absolute_path" "$config_path" > /dev/null 2>&1; then
       log debug "[merge_tree] Files match"
     else
       log debug "[merge_tree] Files differ"
-      strategy="$(ask "Differs: $(tildify "$absolute_path")" \
-        "Overwrite system,Overwrite configuration,Show difference")"
+      local prompt_verb="Differs"
+        local prompt_options="Overwrite system,Overwrite configuration,Show difference"
+      if ! [ -f "$absolute_path" ]; then
+        local prompt_verb="In configuration only"
+        local prompt_options="Copy to system"
+      fi
+      strategy="$(ask "$prompt_verb: $(tildify "$absolute_path")" "$prompt_options")" ||
+        file_merge_tree "$base_files"
       log debug "[merge_tree] Chosen strategy: $strategy"
 
-      if [ "$strategy" -eq 1 ]; then
+      if [ "$strategy" -eq 0 ]; then
+        return 0
+      elif [ "$strategy" -eq 1 ]; then
         cp -vi "$config_path" "$absolute_path"
+        return 1
       elif [ "$strategy" -eq 2 ]; then
         cp -vi "$absolute_path" "$config_path"
+        return 1
       elif [ "$strategy" -eq 3 ]; then
         echo "< $(tildify "$absolute_path") | $(echo "$config_path" | sed "s*$CONFIG_ROOT/**") >"
-        diff "$absolute_path" "$config_path" || return 0
+        diff "$absolute_path" "$config_path"
+        return 1
       else
         log user 'Invalid choice'
       fi