diff --git a/app/models/bot/smooch.rb b/app/models/bot/smooch.rb
index 765a8363c..136f065c1 100644
--- a/app/models/bot/smooch.rb
+++ b/app/models/bot/smooch.rb
@@ -835,7 +835,9 @@ def self.save_text_message(message)
         end
       else
         extra = { url: link.url }
-        pm = ProjectMedia.joins(:media).where('medias.url' => link.url, 'project_medias.team_id' => team.id).last
+        # Normalized url before query DB
+        url_from_pender = Link.normalized(link.url, team.get_pender_key)
+        pm = ProjectMedia.joins(:media).where('medias.url' => url_from_pender, 'project_medias.team_id' => team.id).last
       end
       if pm.nil?
         type = link.nil? ? 'Claim' : 'Link'
diff --git a/app/models/concerns/smooch_messages.rb b/app/models/concerns/smooch_messages.rb
index 2e8a2d590..140670c39 100644
--- a/app/models/concerns/smooch_messages.rb
+++ b/app/models/concerns/smooch_messages.rb
@@ -426,12 +426,15 @@ def relate_item_and_caption(message, associated, app_id, author, request_type, a
       target = self.create_project_media_from_message(message)
       unless target.nil?
         smoooch_post_save_message_actions(message, target, app_id, author, request_type, associated_obj)
-        r = Relationship.new
-        r.skip_check_ability = true
-        r.relationship_type = Relationship.suggested_type
-        r.source_id = associated.id
-        r.target_id = target.id
-        r.save!
+        r_exists = Relationship.where(source_id: associated.id, target_id: target.id).exists?
+        unless r_exists
+          r = Relationship.new
+          r.skip_check_ability = true
+          r.relationship_type = Relationship.suggested_type
+          r.source_id = associated.id
+          r.target_id = target.id
+          r.save!
+        end
       end
     end