diff --git a/app/javascript/dashboard/helper/filterQueryGenerator.js b/app/javascript/dashboard/helper/filterQueryGenerator.js
index d70a30a6b..b2eff3d84 100644
--- a/app/javascript/dashboard/helper/filterQueryGenerator.js
+++ b/app/javascript/dashboard/helper/filterQueryGenerator.js
@@ -1,21 +1,34 @@
 const setArrayValues = item => {
   return item.values[0]?.id ? item.values.map(val => val.id) : item.values;
 };
+
+const generateValues = item => {
+  if (item.attribute_key === 'content') {
+    const values = item.values || '';
+    return values.split(',');
+  }
+  if (Array.isArray(item.values)) {
+    return setArrayValues(item);
+  }
+  if (typeof item.values === 'object') {
+    return [item.values.id];
+  }
+  if (!item.values) {
+    return [];
+  }
+  return [item.values];
+};
+
 const generatePayload = data => {
   // Make a copy of data to avoid vue data reactivity issues
   const filters = JSON.parse(JSON.stringify(data));
   let payload = filters.map(item => {
-    if (Array.isArray(item.values)) {
-      item.values = setArrayValues(item);
-    } else if (typeof item.values === 'object') {
-      item.values = [item.values.id];
-    } else if (!item.values) {
-      item.values = [];
-    } else {
-      item.values = [item.values];
-    }
+    // If item key is content, we will split it using comma and return as array
+    // FIX ME: Make this generic option instead of using the key directly here
+    item.values = generateValues(item);
     return item;
   });
+
   // For every query added, the query_operator is set default to and so the
   // last query will have an extra query_operator, this would break the api.
   // Setting this to null for all query payload
diff --git a/app/javascript/dashboard/mixins/automations/methodsMixin.js b/app/javascript/dashboard/mixins/automations/methodsMixin.js
index 611d5ad38..723cef22c 100644
--- a/app/javascript/dashboard/mixins/automations/methodsMixin.js
+++ b/app/javascript/dashboard/mixins/automations/methodsMixin.js
@@ -199,6 +199,12 @@ export default {
             values: condition.values[0],
           };
         }
+        if (inputType === 'comma_separated_plain_text') {
+          return {
+            ...condition,
+            values: condition.values.join(','),
+          };
+        }
         return {
           ...condition,
           query_operator: condition.query_operator || 'and',
diff --git a/app/javascript/dashboard/routes/dashboard/settings/automation/EditAutomationRule.vue b/app/javascript/dashboard/routes/dashboard/settings/automation/EditAutomationRule.vue
index 74dac7cf9..3ac454868 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/automation/EditAutomationRule.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/automation/EditAutomationRule.vue
@@ -52,7 +52,7 @@
             {{ $t('AUTOMATION.ADD.FORM.CONDITIONS.LABEL') }}
           </label>
           <div
-            class="w-full w-full p-4 bg-slate-25 dark:bg-slate-700 rounded-lg border border-solid border-slate-50 dark:border-slate-700 mb-4"
+            class="w-full p-4 bg-slate-25 dark:bg-slate-700 rounded-lg border border-solid border-slate-50 dark:border-slate-700 mb-4"
           >
             <filter-input-box
               v-for="(condition, i) in automation.conditions"
@@ -94,7 +94,7 @@
             {{ $t('AUTOMATION.ADD.FORM.ACTIONS.LABEL') }}
           </label>
           <div
-            class="w-full w-full p-4 bg-slate-25 dark:bg-slate-700 rounded-lg border border-solid border-slate-50 dark:border-slate-700 mb-4"
+            class="w-full p-4 bg-slate-25 dark:bg-slate-700 rounded-lg border border-solid border-slate-50 dark:border-slate-700 mb-4"
           >
             <automation-action-input
               v-for="(action, i) in automation.actions"
diff --git a/app/javascript/dashboard/routes/dashboard/settings/automation/constants.js b/app/javascript/dashboard/routes/dashboard/settings/automation/constants.js
index fc98e315a..9fcee3f45 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/automation/constants.js
+++ b/app/javascript/dashboard/routes/dashboard/settings/automation/constants.js
@@ -19,7 +19,7 @@ export const AUTOMATIONS = {
         key: 'content',
         name: 'Message Content',
         attributeI18nKey: 'MESSAGE_CONTAINS',
-        inputType: 'plain_text',
+        inputType: 'comma_separated_plain_text',
         filterOperators: OPERATOR_TYPES_2,
       },
       {
diff --git a/app/services/filter_service.rb b/app/services/filter_service.rb
index 0254db1a7..c53dbf8a2 100644
--- a/app/services/filter_service.rb
+++ b/app/services/filter_service.rb
@@ -23,8 +23,8 @@ class FilterService
       @filter_values["value_#{current_index}"] = filter_values(query_hash)
       equals_to_filter_string(query_hash[:filter_operator], current_index)
     when 'contains', 'does_not_contain'
-      @filter_values["value_#{current_index}"] = "%#{string_filter_values(query_hash)}%"
-      like_filter_string(query_hash[:filter_operator], current_index)
+      @filter_values["value_#{current_index}"] = values_for_ilike(query_hash)
+      ilike_filter_string(query_hash[:filter_operator], current_index)
     when 'is_present'
       @filter_values["value_#{current_index}"] = 'IS NOT NULL'
     when 'is_not_present'
@@ -47,8 +47,6 @@ class FilterService
       query_hash['values'].map { |x| Conversation.statuses[x.to_sym] }
     when 'message_type'
       query_hash['values'].map { |x| Message.message_types[x.to_sym] }
-    when 'content'
-      string_filter_values(query_hash)
     else
       case_insensitive_values(query_hash)
     end
@@ -62,6 +60,15 @@ class FilterService
     end
   end
 
+  def values_for_ilike(query_hash)
+    if query_hash['values'].is_a?(Array)
+      query_hash['values']
+        .map { |item| "%#{item.strip}%" }
+    else
+      ["%#{query_hash['values'].strip}%"]
+    end
+  end
+
   def string_filter_values(query_hash)
     return query_hash['values'][0].downcase if query_hash['values'].is_a?(Array)
 
@@ -149,6 +156,12 @@ class FilterService
     "NOT IN (:value_#{current_index})"
   end
 
+  def ilike_filter_string(filter_operator, current_index)
+    return "ILIKE ANY (ARRAY[:value_#{current_index}])" if %w[contains].include?(filter_operator)
+
+    "NOT ILIKE ALL (ARRAY[:value_#{current_index}])"
+  end
+
   def like_filter_string(filter_operator, current_index)
     return "LIKE :value_#{current_index}" if %w[contains starts_with].include?(filter_operator)
 
diff --git a/spec/services/conversations/filter_service_spec.rb b/spec/services/conversations/filter_service_spec.rb
index ff0574465..d5f0170ee 100644
--- a/spec/services/conversations/filter_service_spec.rb
+++ b/spec/services/conversations/filter_service_spec.rb
@@ -10,7 +10,6 @@ describe Conversations::FilterService do
   let!(:campaign_2) { create(:campaign, title: 'Campaign', account: account) }
   let!(:inbox) { create(:inbox, account: account, enable_auto_assignment: false) }
 
-  let!(:unassigned_conversation) { create(:conversation, account: account, inbox: inbox) }
   let!(:user_2_assigned_conversation) { create(:conversation, account: account, inbox: inbox, assignee: user_2) }
   let!(:en_conversation_1) do
     create(:conversation, account: account, inbox: inbox, assignee: user_1, campaign_id: campaign_1.id,
@@ -75,7 +74,7 @@ describe Conversations::FilterService do
         params[:payload] = payload
         result = filter_service.new(params, user_1).perform
         conversations = Conversation.where("additional_attributes ->> 'browser_language' IN (?) AND status IN (?)", ['en'], [1, 2])
-        expect(result.length).to be conversations.count
+        expect(result[:count][:all_count]).to be conversations.count
       end
 
       it 'filter conversations by additional_attributes and status with pagination' do
@@ -83,7 +82,45 @@ describe Conversations::FilterService do
         params[:page] = 2
         result = filter_service.new(params, user_1).perform
         conversations = Conversation.where("additional_attributes ->> 'browser_language' IN (?) AND status IN (?)", ['en'], [1, 2])
-        expect(result.length).to be conversations.count
+        expect(result[:count][:all_count]).to be conversations.count
+      end
+
+      it 'filters items with contains filter_operator with values being an array' do
+        params[:payload] = [{
+          attribute_key: 'browser_language',
+          filter_operator: 'contains',
+          values: %w[tr fr],
+          query_operator: '',
+          custom_attribute_type: ''
+        }.with_indifferent_access]
+
+        create(:conversation, account: account, inbox: inbox, assignee: user_1, campaign_id: campaign_1.id,
+                              status: 'pending', additional_attributes: { 'browser_language': 'fr' })
+        create(:conversation, account: account, inbox: inbox, assignee: user_1, campaign_id: campaign_1.id,
+                              status: 'pending', additional_attributes: { 'browser_language': 'tr' })
+
+        result = filter_service.new(params, user_1).perform
+        expect(result[:count][:all_count]).to be 2
+      end
+
+      it 'filters items with does not contain filter operator with values being an array' do
+        params[:payload] = [{
+          attribute_key: 'browser_language',
+          filter_operator: 'does_not_contain',
+          values: %w[tr en],
+          query_operator: '',
+          custom_attribute_type: ''
+        }.with_indifferent_access]
+
+        create(:conversation, account: account, inbox: inbox, assignee: user_1, campaign_id: campaign_1.id,
+                              status: 'pending', additional_attributes: { 'browser_language': 'fr' })
+        create(:conversation, account: account, inbox: inbox, assignee: user_1, campaign_id: campaign_1.id,
+                              status: 'pending', additional_attributes: { 'browser_language': 'tr' })
+
+        result = filter_service.new(params, user_1).perform
+
+        expect(result[:count][:all_count]).to be 1
+        expect(result[:conversations].first.additional_attributes['browser_language']).to eq 'fr'
       end
 
       it 'filter conversations by additional_attributes with NOT_IN filter' do
@@ -98,7 +135,7 @@ describe Conversations::FilterService do
       end
 
       it 'filter conversations by tags' do
-        unassigned_conversation.update_labels('support')
+        user_2_assigned_conversation.update_labels('support')
         params[:payload] = [
           {
             attribute_key: 'assignee_id',
@@ -119,7 +156,7 @@ describe Conversations::FilterService do
           }.with_indifferent_access
         ]
         result = filter_service.new(params, user_1).perform
-        expect(result.length).to be 2
+        expect(result[:count][:all_count]).to be 1
       end
 
       it 'filter conversations by is_present filter_operator' do