diff --git a/tools/release/generate_release_notes.rb b/tools/release/generate_release_notes.rb
index 59a9cad98..301accda8 100755
--- a/tools/release/generate_release_notes.rb
+++ b/tools/release/generate_release_notes.rb
@@ -39,12 +39,15 @@ current_release_dashes = current_release.tr(".", "-")
 
 release_notes = IO.read(RELEASE_NOTES_PATH).split("\n")
 
-release_notes.insert(5, "* <<logstash-#{current_release_dashes},Logstash #{current_release}>>")
+current_release_heading = "* <<logstash-#{current_release_dashes},Logstash #{current_release}>>"
+release_notes.insert(5, current_release_heading) unless release_notes[5].eql?(current_release_heading)
 
-release_notes_entry_index = release_notes.find_index {|line| line.match(/^\[\[logstash/) }
+coming_tag_index = release_notes.find_index {|line| line.match(/^coming\[#{current_release}\]/) }
+coming_tag_index += 1 if coming_tag_index
+release_notes_entry_index = coming_tag_index || release_notes.find_index {|line| line.match(/^\[\[logstash/) }
 
-report << "[[logstash-#{current_release_dashes}]]"
-report << "=== Logstash #{current_release} Release Notes\n"
+report << "[[logstash-#{current_release_dashes}]]" unless release_notes.any? { |line| line.match(/^\[\[logstash-#{current_release_dashes}/) }
+report << "=== Logstash #{current_release} Release Notes\n" unless release_notes.any? { |line| line.match(/^=== Logstash #{current_release}/)}
 
 plugin_changes = {}