diff --git a/.github/workflows/update-api-components.yml b/.github/workflows/update-api-components.yml
index 42cc1d2827..c4377267a4 100644
--- a/.github/workflows/update-api-components.yml
+++ b/.github/workflows/update-api-components.yml
@@ -24,7 +24,7 @@ jobs:
       - run: bundle install
 
       - name: Download spec and insert into documentation
-        run: bundle exec jekyll spec-insert
+        run: bundle exec jekyll spec-insert -F -R
 
       - name: Get current date
         id: date
diff --git a/DEVELOPER_GUIDE.md b/DEVELOPER_GUIDE.md
index 13b172273a..d81038ef5b 100644
--- a/DEVELOPER_GUIDE.md
+++ b/DEVELOPER_GUIDE.md
@@ -49,7 +49,13 @@ bundle exec jekyll spec-insert
 If you are working on multiple Markdown files and do not want to keep running the `jekyll spec-insert` command, you can add the `--watch` (or `-W`) flag to the command to watch for changes in the Markdown files and automatically render the API components:
 
 ```shell
-bundle exec jekyll spec-insert --watch
+bundle exec jekyll spec-insert -W
+```
+
+By default, when the plugin encounters an error when processing a file, the plugin prints out the error than moves on to the next file. If you want it to short-circuit when an error occurs, add the `--fail-on-error` (or `-F`) flag to the command:
+
+```shell
+bundle exec jekyll spec-insert -F
 ```
 
 Depending on the text editor you are using, you may need to manually reload the file from disk to see the changes applied by the plugin if the editor does not automatically reload the file periodically.
diff --git a/spec-insert/config.yml b/spec-insert/config.yml
index 78c982c77c..a160642965 100644
--- a/spec-insert/config.yml
+++ b/spec-insert/config.yml
@@ -8,4 +8,6 @@ param_table:
 # Replace text in every description in the spec file
 text_replacements:
   - replace: "https://opensearch.org/docs/latest"
-    with: "{{site.url}}{{site.baseurl}}"
\ No newline at end of file
+    with: "{{site.url}}{{site.baseurl}}"
+  - replace: "\n"
+    with: " "
\ No newline at end of file
diff --git a/spec-insert/lib/doc_processor.rb b/spec-insert/lib/doc_processor.rb
index 0aaa01061a..3cddb5939c 100644
--- a/spec-insert/lib/doc_processor.rb
+++ b/spec-insert/lib/doc_processor.rb
@@ -17,7 +17,6 @@ def initialize(file_path, logger:)
   # Processes the file, replacing spec-insert blocks with rendered content
   # @param [Boolean] write_to_file Whether to write the changes back to the file
   def process(write_to_file: true)
-    relative_path = @file_path.relative_path_from(Pathname.new(Dir.pwd))
     lines = File.readlines(@file_path)
     original_content = lines.join
     insertions = find_insertions(lines)
@@ -27,11 +26,10 @@ def process(write_to_file: true)
     rendered_content = lines.join
     if write_to_file && rendered_content != original_content
       File.write(@file_path, rendered_content)
-      @logger.info "Spec components inserted into #{relative_path} successfully."
+      relative_path = @file_path.relative_path_from(Pathname.new(Dir.pwd))
+      @logger.info "Successfully updated #{relative_path}."
     end
     rendered_content
-  rescue SpecInsertError => e
-    @logger.error "Error processing #{relative_path}. #{e.message}"
   end
 
   private
diff --git a/spec-insert/lib/jekyll-spec-insert.rb b/spec-insert/lib/jekyll-spec-insert.rb
index 14a8997cc8..6c4c1fb078 100644
--- a/spec-insert/lib/jekyll-spec-insert.rb
+++ b/spec-insert/lib/jekyll-spec-insert.rb
@@ -14,13 +14,14 @@ def self.init_with_program(prog)
       c.syntax 'spec-insert [options]'
       c.option 'watch', '--watch', '-W', 'Watch for changes and rebuild'
       c.option 'refresh-spec', '--refresh-spec', '-R', 'Redownload the OpenSearch API specification'
+      c.option 'fail-on-error', '--fail-on-error', '-F', 'Fail on error'
       c.action do |_args, options|
         spec_file = File.join(Dir.pwd, 'spec-insert/opensearch-openapi.yaml')
         excluded_paths = YAML.load_file('_config.yml')['exclude']
         download_spec(spec_file, forced: options['refresh-spec'])
         SpecHash.load_file(spec_file)
-        run_once(excluded_paths)
-        watch(excluded_paths) if options['watch']
+        run_once(excluded_paths, fail_on_error: options['fail-on-error'])
+        watch(excluded_paths, fail_on_error: options['fail-on-error']) if options['watch']
       end
     end
   end
@@ -34,19 +35,27 @@ def self.download_spec(spec_file, forced: false)
            "-o #{spec_file}"
   end
 
-  def self.run_once(excluded_paths)
+  def self.process_file(file, fail_on_error: false)
+    DocProcessor.new(file, logger: Jekyll.logger).process
+  rescue StandardError => e
+    raise e if fail_on_error
+    relative_path = Pathname(file).relative_path_from(Pathname.new(Dir.pwd))
+    Jekyll.logger.error "Error processing #{relative_path}: #{e.message}"
+  end
+
+  def self.run_once(excluded_paths, fail_on_error: false)
     excluded_paths = excluded_paths.map { |path| File.join(Dir.pwd, path) }
     Dir.glob(File.join(Dir.pwd, '**/*.md'))
        .filter { |file| excluded_paths.none? { |excluded| file.start_with?(excluded) } }
-       .each { |file| DocProcessor.new(file, logger: Jekyll.logger).process }
+       .each { |file| process_file(file, fail_on_error: fail_on_error) }
   end
 
-  def self.watch(excluded_paths)
+  def self.watch(excluded_paths, fail_on_error: false)
     Jekyll.logger.info "\nWatching for changes...\n"
     excluded_paths = excluded_paths.map { |path| /\.#{path}$/ }
 
     Listen.to(Dir.pwd, only: /\.md$/, ignore: excluded_paths) do |modified, added, _removed|
-      (modified + added).each { |file| DocProcessor.new(file, logger: Jekyll.logger).process }
+      (modified + added).each { |file| process_file(file, fail_on_error: fail_on_error) }
     end.start
 
     trap('INT') { exit }
diff --git a/spec-insert/lib/renderers/parameter_table_renderer.rb b/spec-insert/lib/renderers/parameter_table_renderer.rb
index 2ab439be5c..e07e820c29 100644
--- a/spec-insert/lib/renderers/parameter_table_renderer.rb
+++ b/spec-insert/lib/renderers/parameter_table_renderer.rb
@@ -60,7 +60,7 @@ def row(param)
   def description(param)
     deprecation = deprecation(param)
     required = param.required && @columns.exclude?('Required') ? '**(Required)** ' : ''
-    description = param.description.gsub("\n", ' ')
+    description = param.description
     valid_values = valid_values(param)
     default = param.default.nil? || @columns.include?('Default') ? '' : " _(Default: `#{param.default}`)_"
 
diff --git a/spec-insert/spec/mock_config.yml b/spec-insert/spec/mock_config.yml
index 9b7b5c9c59..15e31f24ea 100644
--- a/spec-insert/spec/mock_config.yml
+++ b/spec-insert/spec/mock_config.yml
@@ -8,5 +8,7 @@ param_table:
 text_replacements:
   - replace: "https://opensearch.org/docs/latest"
     with: "{{site.url}}{{site.baseurl}}"
+  - replace: "\n"
+    with: " "
   - replace: master node
     with: cluster manager node
\ No newline at end of file