diff --git a/app/assets/stylesheets/shared/_icons.scss b/app/assets/stylesheets/shared/_icons.scss
new file mode 100644
index 000000000..d63fbacbf
--- /dev/null
+++ b/app/assets/stylesheets/shared/_icons.scss
@@ -0,0 +1,11 @@
+.fa-check {
+  color: $green;
+}
+
+.fa-info-circle {
+  color: $blue;
+}
+
+.fa-times {
+  color: $red;
+}
diff --git a/app/assets/stylesheets/shared/_validations.scss b/app/assets/stylesheets/shared/_validations.scss
index 5dcb09dcf..dec75f637 100644
--- a/app/assets/stylesheets/shared/_validations.scss
+++ b/app/assets/stylesheets/shared/_validations.scss
@@ -1,29 +1,18 @@
 .validation {
-  .fa-check {
-    color: $green;
-  }
-
-  .fa-info-circle {
-    color: $blue;
-  }
-
-  .fa-times {
-    color: $red;
-  }
-
   &.validation-feed {
     .validation-list {
+      list-style-type: none;
       margin: 1rem 0 0;
       padding: 0;
 
       li {
         i {
-          margin-right: .15rem;
+          margin-right: 0.15rem;
         }
 
         .text-error {
           font-size: 90%;
-          margin: 0 0 .5rem 1.3rem;
+          margin: 0 0 0.5rem 1.6rem;
         }
 
         &:last-of-type .text-error {
diff --git a/app/assets/stylesheets/tylium.scss b/app/assets/stylesheets/tylium.scss
index cba0d31e5..64cdfcd2c 100644
--- a/app/assets/stylesheets/tylium.scss
+++ b/app/assets/stylesheets/tylium.scss
@@ -23,6 +23,7 @@
 @import 'shared/datatables';
 @import 'shared/editor_toolbar';
 @import 'shared/empty_state.scss';
+@import 'shared/icons';
 @import 'shared/inline_editable';
 @import 'shared/mixins';
 @import 'shared/noscript';
diff --git a/app/assets/stylesheets/tylium/modules/_buttons.scss b/app/assets/stylesheets/tylium/modules/_buttons.scss
index bd7ee3bf4..fcad08a51 100644
--- a/app/assets/stylesheets/tylium/modules/_buttons.scss
+++ b/app/assets/stylesheets/tylium/modules/_buttons.scss
@@ -49,6 +49,23 @@
   }
 }
 
+.btn-link {
+  background-color: transparent;
+  border: none;
+  color: $linkColor;
+  padding: 0;
+  text-decoration: none;
+
+  &:active,
+  &:focus,
+  &:hover,
+  &:not(:disabled):not(.disabled):active {
+    background-color: transparent;
+    box-shadow: none !important;
+    color: $linkColorHover;
+  }
+}
+
 .btn-placeholder {
   align-items: center;
   background-color: $primaryColor;
diff --git a/app/assets/stylesheets/tylium/modules/_dots-menu.scss b/app/assets/stylesheets/tylium/modules/_dots-menu.scss
index 00ef9293c..416083b4b 100644
--- a/app/assets/stylesheets/tylium/modules/_dots-menu.scss
+++ b/app/assets/stylesheets/tylium/modules/_dots-menu.scss
@@ -10,7 +10,7 @@
 
   .dots-dropdown-header {
     font-weight: 400 !important;
-    
+
     &:hover {
       color: $linkColor !important;
       background-color: initial !important;
@@ -21,6 +21,10 @@
       margin-top: 0.3rem;
       padding-top: 0.3rem;
     }
+
+    &:not(:has(+ .dropdown-item)) {
+      display: none;
+    }
   }
 
   .dropdown-menu {
diff --git a/app/assets/stylesheets/tylium/modules/_modals.scss b/app/assets/stylesheets/tylium/modules/_modals.scss
index b58a016b6..aa4b5069d 100644
--- a/app/assets/stylesheets/tylium/modules/_modals.scss
+++ b/app/assets/stylesheets/tylium/modules/_modals.scss
@@ -1,16 +1,16 @@
 .modal {
-
   .modal-dialog {
-    max-width: 560px;
+    &:not(.modal-lg, .modal-xl) {
+      max-width: 560px;
+    }
 
     .modal-content {
       font-size: 0.9rem;
 
       .modal-body {
-
         .add_multiple_nodes_form {
           display: none;
-        
+
           .add_multiple_nodes_error {
             display: none;
             color: #b94a48;
@@ -49,7 +49,6 @@
   }
 
   &#modal_delete_node {
-
     ul {
       list-style: disc;
       padding-left: 30px;
@@ -70,7 +69,7 @@
         text-decoration: underline !important;
       }
     }
-    
+
     .invalid-selection {
       cursor: not-allowed;
     }
@@ -109,13 +108,12 @@
   }
 
   &#try-pro {
-    
     .modal-dialog {
       max-width: 80%;
-  
+
       .modal-body {
         height: 80vh;
-    
+
         iframe {
           border: none;
           top: 0;
@@ -125,7 +123,7 @@
           width: 100%;
         }
       }
-  
+
       .modal-header h5 span {
         color: $primaryColor;
       }
diff --git a/app/models/concerns/has_fields.rb b/app/models/concerns/has_fields.rb
index 27875cd6d..61ff4dafb 100644
--- a/app/models/concerns/has_fields.rb
+++ b/app/models/concerns/has_fields.rb
@@ -11,13 +11,22 @@ def local_fields
   # Extract a Title file if one exists.
   def title
     fields.fetch(
-      "Title",
-      "(No #[Title]# field)"
+      'Title',
+      '(No #[Title]# field)'
     )
   end
 
   def title?
-    fields["Title"].present?
+    fields['Title'].present?
+  end
+
+  private
+
+  def update_container(container_field, updated_fields)
+    self.send(
+      :"#{container_field}=",
+      FieldParser.fields_hash_to_source(updated_fields)
+    )
   end
 
   module ClassMethods
@@ -52,14 +61,17 @@ def dradis_has_fields_for(container_field)
       define_method :set_field do |field, value|
         # Don't use 'fields' as a local variable name or it conflicts with the
         # #fields getter method
-        updated_fields        = fields
+        updated_fields = fields
         updated_fields[field] = value
-        self.send(
-          :"#{container_field}=",
-          updated_fields.to_a.map { |h| "#[#{h[0]}]#\n#{h[1]}" }.join("\n\n")
-        )
+        self.update_container(container_field, updated_fields)
+      end
+
+      # Completely removes the field (field header and value) from the content
+      define_method :delete_field do |field|
+        updated_fields = fields
+        updated_fields.except!(field)
+        self.update_container(container_field, updated_fields)
       end
     end
   end
-
 end
diff --git a/app/models/field_parser.rb b/app/models/field_parser.rb
index cb743aa15..3b5de25fd 100644
--- a/app/models/field_parser.rb
+++ b/app/models/field_parser.rb
@@ -1,19 +1,15 @@
 class FieldParser
   FIELDS_REGEX = /#\[(.+?)\]#[\r|\n](.*?)(?=#\[|\z)/m
-  FIELDLESS_REGEX = /^([\s\S]*?)(?=\n{,2}#\[.+?\]#|\z)/
+  HEADERLESS_REGEX = /^([\s\S]*?)(?=\n{,2}#\[.+?\]#|\z)/
 
   # Convert serialized form data to Dradis-style item content.
   def self.fields_to_source(serialized_form)
-    serialized_form.each_slice(2).map do |field_name, field_value|
-      field = field_name[:value]
-      value = field_value[:value]
-
-      str = ''
-      str << "#[#{field}]#\n" unless field.empty?
-      str << "#{value}" unless value.empty?
+    serialized_form.each_slice(2).map(&to_source).compact.join("\n\n")
+  end
 
-      str
-    end.compact.join("\n\n")
+  # Convert a hash of field name/value pairs to Dradis-style item content.
+  def self.fields_hash_to_source(fields)
+    fields.map(&to_source).compact.join("\n\n")
   end
 
   # Parse the contents of the field and split it to return a Hash of field
@@ -38,7 +34,7 @@ def self.source_to_fields(string)
   #   #[Description]#
   #   Lorem ipsum...
   #
-  # If the string contains a fieldless string, it will be prepended to
+  # If the string contains a headerless field, it will be prepended to
   # the result. E.g.
   #
   #   Line 1
@@ -54,18 +50,33 @@ def self.source_to_fields_array(string)
       field.map(&:strip)
     end
 
-    fieldless_string = parse_fieldless_string(string)
+    headerless_fields = parse_fields_without_headers(string)
 
-    if fieldless_string.present?
-      array.prepend(['', fieldless_string])
+    if headerless_fields.present?
+      array.prepend(['', headerless_fields])
     end
 
     array
   end
 
-  # Field-less strings are strings that do not have a field header (#[Field]#).
+  # Headerless fields are strings that do not have a field header (#[Field]#).
   # This parses all characters before a field header or end of string.
-  def self.parse_fieldless_string(source)
-    source[FIELDLESS_REGEX, 1]
+  def self.parse_fields_without_headers(source)
+    source[HEADERLESS_REGEX, 1]
+  end
+
+  private
+
+  def self.to_source
+    return Proc.new do |field, value|
+      field = field.is_a?(String) ? field.to_s : field[:value]
+      value = value.is_a?(String) ? value.to_s : value[:value]
+
+      str = ''
+      str << "#[#{field}]#\n" unless field.empty?
+      str << value unless value.empty?
+
+      str
+    end
   end
 end
diff --git a/app/services/diffed_content.rb b/app/services/diffed_content.rb
new file mode 100644
index 000000000..9a46c6894
--- /dev/null
+++ b/app/services/diffed_content.rb
@@ -0,0 +1,120 @@
+class DiffedContent
+  EXCLUDED_FIELDS = %w(id plugin plugin_id AddonTags)
+
+  attr_reader :source, :target
+
+  def initialize(source, target)
+    @source = source
+    @target = target
+
+    normalize_content(@source)
+    normalize_content(@target)
+  end
+
+  def content_diff
+    diff_by_word(source.content, target.content)
+  end
+
+  # Lists the fields that have changed between the source and the target and
+  # saves the diffed content for each field.
+  #
+  # Returns a hash with the following structure:
+  # { field: { source: <diffed_source_field>, target: <diffed_target_field> } }
+  def unsynced_fields
+    @unsynced_fields ||=
+      begin
+        fields = @source.fields.except(*EXCLUDED_FIELDS).keys |
+          @target.fields.except(*EXCLUDED_FIELDS).keys
+
+        fields.filter_map do |field|
+          source_value = source.fields[field] || ''
+          target_value = target.fields[field] || ''
+
+          if source_value != target_value
+            [field, diff_by_word(source_value, target_value)]
+          end
+        end.to_h
+      end
+  end
+
+  def changed?
+    source.updated_at != target.updated_at &&
+      source.content != target.content
+  end
+
+  def content_for_update(field_params = nil)
+    if field_params
+      {
+        source: content_with_updated_field_from_target(field: field_params, source: @target.reload, target: @source.reload),
+        target: content_with_updated_field_from_target(field: field_params, source: @source.reload, target: @target.reload)
+      }
+    else
+      { source: @target.content, target: @source.content }
+    end
+  end
+
+  private
+
+  # Given a target record, update its field depending on the following cases:
+  # 1) If the source record has the existing field:
+  #   1.1) If the target record also has the existing field, update the value
+  #     with the value from the source record
+  #   1.2) If the target record does not have the field, insert the field
+  #     at the same index where the field is present in the source record
+  # 2) If the source record is missing the field, delete the field in the
+  #   target record
+  def content_with_updated_field_from_target(field:, source:, target:)
+    source_fields = source.fields.keys
+    source_index = source_fields.excluding(*EXCLUDED_FIELDS).index(field)
+
+    # Case 1)
+    if source_fields.include?(field)
+      # Case 1.1)
+      if target.fields.keys.include?(field)
+        target.set_field(field, source.fields[field])
+      # Case 1.2)
+      else
+        updated_fields = target.fields.to_a.insert(source_index, [field, source.fields[field]])
+        FieldParser.fields_hash_to_source(updated_fields.compact)
+      end
+    # Case 2)
+    else
+      target.delete_field(field)
+    end
+  end
+
+  def diff_by_word(source_content, target_content)
+    Differ.format = :html
+    differ_result = Differ.diff_by_word(source_content, target_content)
+
+    output = highlighted_string(differ_result)
+
+    { source: output[1], target: output[0] }
+  end
+
+  def normalize_content(record)
+    fields = record.fields.except(*EXCLUDED_FIELDS)
+
+    record.content =
+      fields.map do |field, value|
+        "#[#{field}]#\n#{value.gsub("\r", '')}\n"
+      end.join("\n")
+  end
+
+  def highlighted_string(differ_result)
+    [:delete, :insert].map do |highlight_type|
+      result_str = differ_result.dup.to_s
+
+      case highlight_type
+      when :delete
+        result_str.gsub!(/<del class="differ">(.*?)<\/del>/m, '<mark>\1</mark>')
+        result_str.gsub!(/<ins class="differ">(.*?)<\/ins>/m, '')
+      when :insert
+        result_str.gsub!(/<ins class="differ">(.*?)<\/ins>/m, '<mark>\1</mark>')
+        result_str.gsub!(/<del class="differ">(.*?)<\/del>/m, '')
+      end
+
+      result_str.html_safe
+    end
+  end
+end
diff --git a/spec/services/diffed_content_spec.rb b/spec/services/diffed_content_spec.rb
new file mode 100644
index 000000000..d2024377c
--- /dev/null
+++ b/spec/services/diffed_content_spec.rb
@@ -0,0 +1,106 @@
+require 'rails_helper'
+
+describe DiffedContent do
+  let(:issue1) { create(:issue, text: "#[Title]#\nIssue1\n") }
+  let(:issue2) { create(:issue, text: "#[Title]#\nIssue2\n") }
+
+  subject { described_class.new(issue1, issue2) }
+
+  describe '#content_diff' do
+    it 'returns the diff' do
+      expect(subject.content_diff).to eq({
+        source: "#[Title]#\n<mark>Issue1</mark>\n",
+        target: "#[Title]#\n<mark>Issue2</mark>\n"
+      })
+    end
+  end
+
+  describe '#changed?' do
+    context 'source and target does not match' do
+      it 'returns true' do
+        issue1.update text: 'test', updated_at: Time.now + 1.day
+        expect(subject.changed?).to eq true
+      end
+    end
+
+    context 'source and target matches' do
+      it 'returns false' do
+        issue1.update text: issue2.content
+        expect(subject.changed?).to eq false
+      end
+    end
+  end
+
+  describe '#unsynced_fields' do
+    it 'returns the fields that have changed between the source and the target' do
+      expect(subject.unsynced_fields).to eq({
+        'Title' => {
+          source: '<mark>Issue1</mark>',
+          target: '<mark>Issue2</mark>'
+        }
+      })
+    end
+  end
+
+  describe '#content_for_update' do
+    context 'field_params is present' do
+      context 'the field is present in both the source and target' do
+        it 'returns the updated content' do
+          expect(subject.content_for_update('Title')).to eq({
+            source: "#[Title]#\n#{issue2.reload.title}",
+            target: "#[Title]#\n#{issue1.reload.title}"
+          })
+        end
+      end
+
+      context 'the field is not present in the source' do
+        before do
+          issue2.update(content: "#[Title]#\nIssue2\n\n#[Description]#\nTest Description\n")
+        end
+
+        it 'returns the updated content' do
+          expect(subject.content_for_update('Description')).to eq({
+            source: "#[Title]#\n#{issue1.reload.title}\n\n#[Description]#\nTest Description",
+            target: "#[Title]#\n#{issue2.reload.title}"
+          })
+        end
+      end
+
+      context 'the field is blank in the issue' do
+        before do
+          issue1.update(content: "#[Title]#\nIssue1\n\n#[Description]#\n\n")
+          issue2.update(content: "#[Title]#\nIssue2\n\n#[Description]#\nTest Description\n")
+        end
+
+        it 'returns the updated content' do
+          expect(subject.content_for_update('Description')).to eq({
+            source: "#[Title]#\n#{issue1.reload.title}\n\n#[Description]#\nTest Description",
+            target: "#[Title]#\n#{issue2.reload.title}\n\n#[Description]#\n"
+          })
+        end
+      end
+
+      context 'the field is found on an index not present in the issue' do
+        before do
+          issue2.update(content: "#[Title]#\nIssue2\n\n#[Description]#\nTest Description\n\n#[Mitigation]#\nTest Mitigation\n")
+        end
+
+        it 'returns the updated content' do
+          expect(subject.content_for_update('Mitigation')).to eq({
+            source: "#[Title]#\n#{issue1.reload.title}\n\n#[Mitigation]#\nTest Mitigation",
+            target: "#[Title]#\n#{issue2.reload.title}\n\n#[Description]#\nTest Description"
+          })
+        end
+      end
+    end
+
+    context 'field_params is not present' do
+      it 'returns the issue and entry content' do
+        expect(subject.content_for_update(nil)).to eq({
+          source: "#[Title]#\n#{issue2.reload.title}\n",
+          target: "#[Title]#\n#{issue1.reload.title}\n"
+        })
+      end
+    end
+  end
+end