Track IP address used for message delivery attempts

.github/workflows/ci.yml

@@ -99,6 +99,10 @@ jobs:
         run: docker compose pull mariadb
         env:
           POSTAL_IMAGE: ghcr.io/modalsource/postal:ci-${{ github.sha }}
+      - name: Prepare database
+        run: docker compose run --rm postal sh -c 'bundle exec rails db:prepare'
+        env:
+          POSTAL_IMAGE: ghcr.io/modalsource/postal:ci-${{ github.sha }}
       - run: docker compose run --rm postal sh -c 'bundle exec rspec'
         env:
           POSTAL_IMAGE: ghcr.io/modalsource/postal:ci-${{ github.sha }}

app/lib/message_dequeuer/base.rb

@@ -62,7 +62,7 @@ def hold_if_server_development_mode
       return unless queued_message.server.mode == "Development"
 
       log "server is in development mode, holding"
-      create_delivery "Held", details: "Server is in development mode."
+      create_delivery "Held", details: "Server is in development mode.", ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -80,7 +80,8 @@ def log_sender_result
                                     output: @result.output&.strip,
                                     sent_with_ssl: @result.secure,
                                     log_id: @result.log_id,
-                                    time: @result.time
+                                    time: @result.time,
+                                    ip_address_id: queued_message.ip_address_id
     end
 
     def handle_exception(exception)

app/lib/message_dequeuer/outgoing_message_processor.rb

@@ -35,7 +35,7 @@ def check_domain
       return if queued_message.message.domain
 
       log "message has no domain, hard failing"
-      create_delivery "HardFail", details: "Message's domain no longer exist"
+      create_delivery "HardFail", details: "Message's domain no longer exist", ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -44,7 +44,7 @@ def check_rcpt_to
       return unless queued_message.message.rcpt_to.blank?
 
       log "message has no 'to' address, hard failing"
-      create_delivery "HardFail", details: "Message doesn't have an RCPT to"
+      create_delivery "HardFail", details: "Message doesn't have an RCPT to", ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -63,7 +63,7 @@ def hold_if_credential_is_set_to_hold
       return unless queued_message.message.credential.hold?
 
       log "credential wants us to hold messages, holding"
-      create_delivery "Held", details: "Credential is configured to hold all messages authenticated by it."
+      create_delivery "Held", details: "Credential is configured to hold all messages authenticated by it.", ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -73,7 +73,7 @@ def hold_if_recipient_on_suppression_list
       return unless sl = queued_message.server.message_db.suppression_list.get(:recipient, queued_message.message.rcpt_to)
 
       log "recipient is on the suppression list, holding"
-      create_delivery "Held", details: "Recipient (#{queued_message.message.rcpt_to}) is on the suppression list (reason: #{sl['reason']})"
+      create_delivery "Held", details: "Recipient (#{queued_message.message.rcpt_to}) is on the suppression list (reason: #{sl['reason']})", ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -121,7 +121,8 @@ def inspect_message
         log "added recipient to suppression list", recipient: queued_message.message.rcpt_to, reason: "Truemail validation failed"
 
         create_delivery "HardFail",
-                        details: "Email address validation failed: #{result.validation_message}"
+                        details: "Email address validation failed: #{result.validation_message}",
+                        ip_address_id: queued_message.ip_address_id
         remove_from_queue
         stop_processing
         return
@@ -140,7 +141,8 @@ def fail_if_spam
       log "message is spam (#{queued_message.message.spam_score}), hard failing", server_threshold: queued_message.server.outbound_spam_threshold
       create_delivery "HardFail",
                       details: "Message is likely spam. Threshold is #{queued_message.server.outbound_spam_threshold} and " \
-                               "the message scored #{queued_message.message.spam_score}."
+                               "the message scored #{queued_message.message.spam_score}.",
+                      ip_address_id: queued_message.ip_address_id
       remove_from_queue
       stop_processing
     end
@@ -156,7 +158,7 @@ def check_send_limits
         # If we're over the limit, we're going to be holding this message
         log "server send limit has been exceeded, holding", send_limit: queued_message.server.send_limit
         queued_message.server.update_columns(send_limit_exceeded_at: Time.now, send_limit_approaching_at: nil)
-        create_delivery "Held", details: "Message held because send limit (#{queued_message.server.send_limit}) has been reached."
+        create_delivery "Held", details: "Message held because send limit (#{queued_message.server.send_limit}) has been reached.", ip_address_id: queued_message.ip_address_id
         remove_from_queue
         stop_processing
       elsif queued_message.server.send_limit_approaching?

app/views/messages/_deliveries.html.haml

@@ -29,6 +29,8 @@
       .noData.noData--clean
         %h2.noData__text No delivery attempts yet.
   - else
+    - ip_address_ids = message.deliveries.map(&:ip_address_id).compact.uniq
+    - ip_addresses_by_id = IPAddress.where(id: ip_address_ids).index_by(&:id)
     - for delivery in message.deliveries.reverse
       %li.deliveryList__item
         .deliveryList__top
@@ -38,6 +40,14 @@
             - if delivery.sent_with_ssl
               = image_tag 'icons/lock.svg', :class => 'deliveryList__secure'
             %span.label.label--large{:class => "label--messageStatus-#{delivery.status.underscore}"}= delivery.status.underscore.humanize
+        - if delivery.ip_address_id
+          - ip_address = ip_addresses_by_id[delivery.ip_address_id]
+          - if ip_address
+            %p.deliveryList__info
+              %strong IP Address:
+              = ip_address.ipv4
+              - if ip_address.hostname
+                (#{ip_address.hostname})
         - if delivery.details
           %p.deliveryList__error= format_delivery_details(@server, delivery.details)
         - if delivery.log_id || delivery.output

lib/postal/message_db/delivery.rb

@@ -64,7 +64,8 @@ def webhook_hash
           output: output.to_s.dup.force_encoding("UTF-8").scrub.truncate(512),
           sent_with_ssl: sent_with_ssl,
           timestamp: @attributes["timestamp"],
-          time: time
+          time: time,
+          ip_address_id: ip_address_id
         }
       end
 

lib/postal/message_db/migrations/03_create_deliveries.rb

@@ -16,7 +16,9 @@ def up
                                                details: "varchar(512) DEFAULT NULL",
                                                sent_with_ssl: "tinyint(1) DEFAULT 0",
                                                log_id: "varchar(100) DEFAULT NULL",
-                                               timestamp: "decimal(18,6) DEFAULT NULL"
+                                               timestamp: "decimal(18,6) DEFAULT NULL",
+                                               time: "decimal(8,2) DEFAULT NULL",
+                                               ip_address_id: "int(11) DEFAULT NULL"
                                              },
                                              indexes: {
                                                on_message_id: "`message_id`"

lib/postal/message_db/migrations/11_add_time_to_deliveries.rb

@@ -6,6 +6,10 @@ module Migrations
       class AddTimeToDeliveries < Postal::MessageDB::Migration
 
         def up
+          # Check if column already exists (for fresh installs that include it in CREATE TABLE)
+          result = @database.query("SELECT COUNT(*) as count FROM information_schema.COLUMNS WHERE TABLE_SCHEMA = '#{@database.database_name}' AND TABLE_NAME = 'deliveries' AND COLUMN_NAME = 'time'").first
+          return if result["count"] > 0
+
           @database.query("ALTER TABLE `#{@database.database_name}`.`deliveries` ADD COLUMN `time` decimal(8,2)")
         end
 

lib/postal/message_db/migrations/21_add_ip_address_id_to_deliveries.rb

@@ -0,0 +1,23 @@
+# frozen_string_literal: true
+
+module Postal
+  module MessageDB
+    module Migrations
+      class AddIPAddressIdToDeliveries < Postal::MessageDB::Migration
+
+        def up
+          # Check if column already exists (for fresh installs that include it in CREATE TABLE)
+          result = @database.query("SELECT COUNT(*) as count FROM information_schema.COLUMNS WHERE TABLE_SCHEMA = '#{@database.database_name}' AND TABLE_NAME = 'deliveries' AND COLUMN_NAME = 'ip_address_id'").first
+          return if result["count"] > 0
+
+          @database.query("ALTER TABLE `#{@database.database_name}`.`deliveries` ADD COLUMN `ip_address_id` int(11) NULL")
+        end
+
+        def down
+          @database.query("ALTER TABLE `#{@database.database_name}`.`deliveries` DROP COLUMN `ip_address_id`")
+        end
+
+      end
+    end
+  end
+end

spec/lib/message_dequeuer/outgoing_message_processor_spec.rb

@@ -597,6 +597,84 @@ module MessageDequeuer
       end
     end
 
+    context "when ip_address_id is set on the queued message" do
+      let(:organization) { create(:organization) }
+      let(:ip_pool) { create(:ip_pool, :with_ip_address) }
+      let(:ip_address) { ip_pool.ip_addresses.first }
+      let(:server) { create(:server, ip_pool: ip_pool, organization: organization) }
+      let(:queued_message) { create(:queued_message, :locked, message: message, ip_address: ip_address) }
+      let(:send_result) do
+        SendResult.new do |r|
+          r.type = "Sent"
+        end
+      end
+
+      before do
+        organization.ip_pools << ip_pool
+        mocked_sender = double("SMTPSender")
+        allow(mocked_sender).to receive(:send_message).and_return(send_result)
+        allow(state).to receive(:sender_for).and_return(mocked_sender)
+      end
+
+      it "stores ip_address_id in the delivery for Sent status" do
+        processor.process
+        delivery = message.deliveries.last
+        expect(delivery.ip_address_id).to eq(ip_address.id)
+      end
+
+      context "when message has no domain and fails" do
+        let(:message) { MessageFactory.outgoing(server, domain: nil, credential: credential) }
+
+        it "stores ip_address_id in the delivery for HardFail status" do
+          processor.process
+          delivery = message.deliveries.last
+          expect(delivery).to have_attributes(
+            status: "HardFail",
+            ip_address_id: ip_address.id
+          )
+        end
+      end
+
+      context "when message has no rcpt_to and fails" do
+        before do
+          message.update(rcpt_to: "")
+        end
+
+        it "stores ip_address_id in the delivery for HardFail status" do
+          processor.process
+          delivery = message.deliveries.last
+          expect(delivery).to have_attributes(
+            status: "HardFail",
+            ip_address_id: ip_address.id
+          )
+        end
+      end
+
+      context "when message is spam and fails" do
+        before do
+          server.update(outbound_spam_threshold: 5.0)
+          inspection_result = double("Result",
+            spam_score: 6.0,
+            threat: false,
+            threat_message: nil,
+            spam_checks: [],
+            validation_failed: false,
+            validation_message: nil
+          )
+          allow(Postal::MessageInspection).to receive(:scan).and_return(inspection_result)
+        end
+
+        it "stores ip_address_id in the delivery for HardFail status" do
+          processor.process
+          delivery = message.deliveries.last
+          expect(delivery).to have_attributes(
+            status: "HardFail",
+            ip_address_id: ip_address.id
+          )
+        end
+      end
+    end
+
     context "when an exception occurrs during processing" do
       before do
         smtp_sender_mock = double("SMTPSender")