diff --git a/app/controllers/entries_controller.rb b/app/controllers/entries_controller.rb
index 6c7ac395..df440f50 100644
--- a/app/controllers/entries_controller.rb
+++ b/app/controllers/entries_controller.rb
@@ -101,7 +101,7 @@ def create
       if params[:entry][:image].present?
         if @existing_entry.image_url_cdn.present? || params[:entry][:image].count > 1
           image_urls = collage_from_attachments(Array(params[:entry][:image]))
-          ImageCollageJob.perform_later(@existing_entry.id, image_urls)
+          ImageCollageJob.perform_later(@existing_entry.id, urls: image_urls)
         elsif params[:entry][:image].present?
           @existing_entry.image = params[:entry][:image].first
         end
@@ -117,7 +117,7 @@ def create
       @entry = current_user.entries.create(entry_params)
       if params[:entry][:image].present? && params[:entry][:image].count > 1
         image_urls = collage_from_attachments(params[:entry][:image])
-        ImageCollageJob.perform_later(@entry.id, image_urls)
+        ImageCollageJob.perform_later(@entry.id, urls: image_urls)
       elsif params[:entry][:image].present?
         @entry.image = params[:entry][:image].first
       end
@@ -155,7 +155,7 @@ def update
       if params[:entry][:image].present?
         if @existing_entry.image_url_cdn.present? || params[:entry][:image].count > 1
           image_urls = collage_from_attachments(Array(params[:entry][:image]))
-          ImageCollageJob.perform_later(@existing_entry.id, image_urls)
+          ImageCollageJob.perform_later(@existing_entry.id, urls: image_urls)
         else
           @existing_entry.image = params[:entry][:image]
         end
@@ -182,7 +182,7 @@ def update
       if @entry.update(update_params)
         if params[:entry][:image].present? && params[:entry][:image].size > 1
           image_urls = collage_from_attachments(params[:entry][:image])
-          ImageCollageJob.perform_later(@entry.id, image_urls)
+          ImageCollageJob.perform_later(@entry.id, urls: image_urls)
         elsif params[:entry][:image].present?
           @entry.image = params[:entry][:image].first
           @entry.save
diff --git a/app/jobs/image_collage_job.rb b/app/jobs/image_collage_job.rb
index e04b1ae6..950e344e 100644
--- a/app/jobs/image_collage_job.rb
+++ b/app/jobs/image_collage_job.rb
@@ -1,20 +1,82 @@
 class ImageCollageJob < ActiveJob::Base
   queue_as :default
 
-  def perform(entry_id, urls)
+  def perform(entry_id, urls: nil, message_id: nil)
     entry = Entry.where(id: entry_id).first
+    @message_id = message_id
     return nil unless entry.present?
 
     entry.update(filepicker_url: "https://dabble-me.s3.amazonaws.com/uploading.png")
 
-    existing_url = entry&.image_url_cdn == "https://dabble-me.s3.amazonaws.com/uploading.png" ? nil : entry&.image_url_cdn
+    @existing_url = entry&.image_url_cdn == "https://dabble-me.s3.amazonaws.com/uploading.png" ? nil : entry&.image_url_cdn
 
-    filestack_collage_url = collage_from_urls(urls + [existing_url])
+    if @message_id.present?
+      filestack_collage_url = collage_from_mailgun_attachments
+    else
+      filestack_collage_url = collage_from_urls(urls + [@existing_url])
+    end
     entry.update(remote_image_url: filestack_collage_url, filepicker_url: nil)
   end
 
+  def collage_from_mailgun_attachments
+    return unless @message_id.present?
+
+    last_message = nil
+    message = nil
+    5.times do
+      connection = Faraday.new(url: "https://api.mailgun.net") do |f|
+        f.request :json
+        f.response :json
+        f.request :authorization, :basic, 'api', ENV['MAILGUN_API_KEY']
+        f.options.timeout = 120
+        f.options.open_timeout = 120
+      end
+      resp = connection.get("/v3/#{ENV['SMTP_DOMAIN']}/events?pretty=yes&event=accepted&ascending=no&limit=1&message-id=#{@message_id}")
+      last_message = resp.body&.dig("items", 0) if resp.success?
+      break if last_message.present?
+      sleep 10
+    end
+    return unless last_message.present?
+
+    message = nil
+    5.times do
+      message_url = URI.parse(last_message["storage"]["url"])
+      msg_conn = Faraday.new("https://#{message_url.host}") do |f|
+        f.options.timeout = 120
+        f.options.open_timeout = 120
+        f.request :json
+        f.response :json
+        f.request :authorization, :basic, 'api', ENV['MAILGUN_API_KEY']
+      end
+      response = msg_conn.get(message_url.path)
+      message = response.body if response.success?
+      break if message.present?
+      sleep 10
+    end
+    return unless message.present? && message["recipients"].to_s.include?(@user.user_key) || message["from"].to_s.include?(@user.email)
+
+    attachment_urls = message["attachments"].map do |att|
+      next unless att["content-type"]&.downcase.in?(['image/gif', 'image/jpeg', 'image/jpg', 'application/octet-stream', 'image/webp', 'image/png', 'image/heic', 'image/heif'])
+      next unless att["size"].to_i > 20_000
+
+      att["url"].gsub("://", "://api:#{ENV['MAILGUN_API_KEY']}@")
+    end.compact
+    return nil unless attachment_urls.any?
+
+    collage_from_urls(attachment_urls + [@existing_url])
+  end
+
   def collage_from_urls(urls)
+    return nil unless urls.present?
+
+    urls.reject! { |url| url&.include?("googleusercontent.com/mail-sig/") }
     urls.compact!
-    "https://process.filestackapi.com/#{ENV['FILESTACK_API_KEY']}/collage=a:true,i:auto,f:[#{urls[1..-1].map(&:inspect).join(',')}],w:1200,h:1200,m:10/#{CGI.escape(urls.first)}"
+
+    if urls.size == 1 && urls.first.starts_with?("http")
+      urls.first
+    elsif urls.any?
+      first_url = urls.first.include?("%40") ? urls.first : CGI.escape(urls.first) # don't escape if already escaped
+      "https://process.filestackapi.com/#{ENV['FILESTACK_API_KEY']}/collage=a:true,i:auto,f:[#{urls[1..-1].map(&:inspect).join(',')}],w:1200,h:1200,m:10/#{first_url}"
+    end
   end
 end
diff --git a/app/lib/email_processor.rb b/app/lib/email_processor.rb
index 79c5cec8..8f2d23b9 100644
--- a/app/lib/email_processor.rb
+++ b/app/lib/email_processor.rb
@@ -62,7 +62,7 @@ def process
         end
 
         if valid_attachments.size > 1
-          best_attachment_url = collage_from_mailgun_attachments
+          best_attachment_url = "mailgun_collage:#{@message_id}"
         elsif valid_attachments.any?
           best_attachment = valid_attachments.first
         end
@@ -123,13 +123,15 @@ def process
         if existing_entry.image_url_cdn.blank?
           if best_attachment.present?
             existing_entry.image = best_attachment
+          elsif best_attachment_url.present? && best_attachment_url.starts_with?("mailgun_collage:")
+            ImageCollageJob.perform_later(existing_entry.id, message_id: best_attachment_url.gsub("mailgun_collage:", ""))
           elsif best_attachment_url.present?
             existing_entry.remote_image_url = best_attachment_url
           end
         elsif existing_entry.image_url_cdn.present?
           if best_attachment.present?
             image_urls = collage_from_attachments([best_attachment])
-            ImageCollageJob.perform_later(existing_entry.id, image_urls)
+            ImageCollageJob.perform_later(existing_entry.id, urls: image_urls)
           elsif best_attachment_url.present?
             existing_entry.update(filepicker_url: "https://dabble-me.s3.amazonaws.com/uploading.png")
             existing_image = existing_entry.image_url_cdn == "https://dabble-me.s3.amazonaws.com/uploading.png" ? nil : existing_entry.image_url_cdn
@@ -155,6 +157,8 @@ def process
           entry = @user.entries.create!(date: date, inspiration_id: inspiration_id, body: @body, original_email_body: @raw_body)
           if best_attachment.present?
             entry.image = best_attachment
+          elsif best_attachment_url.present? && best_attachment_url.starts_with?("mailgun_collage:")
+            ImageCollageJob.perform_later(entry.id, message_id: best_attachment_url.gsub("mailgun_collage:", ""))
           elsif best_attachment_url.present?
             entry.update(filepicker_url: "https://dabble-me.s3.amazonaws.com/uploading.png")
             entry.remote_image_url = best_attachment_url
@@ -360,45 +364,6 @@ def clean_html_version(html)
     to_utf8(html)
   end
 
-  def collage_from_mailgun_attachments
-    return unless @message_id.present?
-
-    last_message = nil
-    connection = Faraday.new(url: "https://api.mailgun.net") do |f|
-      f.request :json
-      f.response :json
-      f.request :authorization, :basic, 'api', ENV['MAILGUN_API_KEY']
-      f.options.timeout = 20
-      f.options.open_timeout = 20
-    end
-    resp = connection.get("/v3/#{ENV['SMTP_DOMAIN']}/events?pretty=yes&event=accepted&ascending=no&limit=1&message-id=#{@message_id}")
-    last_message = resp.body&.dig("items", 0) if resp.success?
-    return unless last_message.present?
-
-    message = nil
-    message_url = URI.parse(last_message["storage"]["url"])
-    msg_conn = Faraday.new("https://#{message_url.host}") do |f|
-      f.options.timeout = 20
-      f.options.open_timeout = 20
-      f.request :json
-      f.response :json
-      f.request :authorization, :basic, 'api', ENV['MAILGUN_API_KEY']
-    end
-    response = msg_conn.get(message_url.path)
-    message = response.body if response.success?
-    return unless message.present? && message["recipients"].to_s.include?(@user.user_key) || message["from"].to_s.include?(@user.email)
-
-    attachment_urls = message["attachments"].map do |att|
-      next unless att["content-type"]&.downcase.in?(['image/gif', 'image/jpeg', 'image/jpg', 'application/octet-stream', 'image/webp', 'image/png', 'image/heic', 'image/heif'])
-      next unless att["size"].to_i > 20_000
-
-      att["url"].gsub("://", "://api:#{ENV['MAILGUN_API_KEY']}@")
-    end.compact
-    return nil unless attachment_urls.any?
-
-    collage_from_urls(attachment_urls)
-  end
-
   def collage_from_attachments(attachments, existing_image_url: nil)
     return nil unless attachments.present?