diff --git a/R/rules-line-break.R b/R/rules-line-break.R
index a13c11316..b3e56bbcd 100644
--- a/R/rules-line-break.R
+++ b/R/rules-line-break.R
@@ -136,3 +136,33 @@ remove_line_break_in_empty_fun_call <- function(pd) {
   }
   pd
 }
+
+mk_add_line_break_at_pos_id <- function(ids) {
+  ids <- ids
+  
+  function(pd_flat){
+    min_child_ids <- sapply(seq_len(nrow(pd_flat)), function(i){
+      row <- pd_flat[i,]
+      m <- row$pos_id
+      while(!row$terminal){
+        row <- row$child[[1]][1,]
+        m <- min(m, row$pos_id)
+      }
+      m
+    })
+
+    max_child_ids <- sapply(seq_len(nrow(pd_flat)), function(i){
+      row <- pd_flat[i,]
+      m <- row$pos_id
+      while(!row$terminal){
+        row <- row$child[[1]][nrow(row$child[[1]]),]
+        m <- max(m, row$pos_id)
+      }
+      m
+    })
+    
+    nls <- apply(cbind(min_child_ids, max_child_ids), 1 , function(x) sum(ids >= x[1] & ids <= x[2]))
+    pd_flat$lag_newlines <- pd_flat$lag_newlines + nls
+    pd_flat
+  }
+}
diff --git a/R/transform-files.R b/R/transform-files.R
index 737c9281b..f49e013e4 100644
--- a/R/transform-files.R
+++ b/R/transform-files.R
@@ -169,15 +169,34 @@ parse_transform_serialize_r <- function(text, transformers, warn_empty = TRUE) {
     }
     return("")
   }
-  transformed_pd <- apply_transformers(pd_nested, transformers)
-  flattened_pd <- post_visit(transformed_pd, list(extract_terminals)) %>%
-    enrich_terminals(transformers$use_raw_indention) %>%
-    apply_ref_indention() %>%
-    set_regex_indention(
-      pattern = transformers$reindention$regex_pattern,
-      target_indention = transformers$reindention$indention,
-      comments_only = transformers$reindention$comments_only
-    )
+
+  width <- getOption("width")
+
+  newline_ids <- integer(0)
+  tf <- transformers
+  repeat{
+    add_line_break_at_pos_id <- mk_add_line_break_at_pos_id(newline_ids)
+    tf$line_break <- c(lst(add_line_break_at_pos_id),transformers$line_break)
+    transformed_pd <- apply_transformers(pd_nested, tf)
+    
+    flattened_pd <- post_visit(transformed_pd, list(extract_terminals)) %>%
+      enrich_terminals(transformers$use_raw_indention) %>%
+      apply_ref_indention() %>%
+      set_regex_indention(
+        pattern          = transformers$reindention$regex_pattern,
+        target_indention = transformers$reindention$indention,
+        comments_only    = transformers$reindention$comments_only
+      )
+    
+    overflowed <- flattened_pd$pos_id[flattened_pd$col2>width]
+    
+    if(length(overflowed)){
+      newline_ids <- unique(c(newline_ids, min(overflowed)))
+    }else{
+      break
+    }
+  }
+
   serialized_transformed_text <-
     serialize_parse_data_flattened(flattened_pd, start_line = start_line)