diff --git a/.env.sample b/.env.sample
index 7edea10b9..b00d264b2 100644
--- a/.env.sample
+++ b/.env.sample
@@ -50,7 +50,9 @@
 #          The application must have its OAuth2 redirect URI set to ${JOINER_BASE_URL}/callback.
 #          You also need to fill out all the JOINER_* environment variables below.
 #
-# COMPOSE_PROFILES=discord
+# datadog: Start the datadog agent to push performance metrics through ddtrace.
+#          You also need to fill out the DD_API_KEY environment variables below.
+# COMPOSE_PROFILES=discord,datadog
 
 # Change the ports that are forwarded by docker to avoid potential conflicts
 
@@ -64,3 +66,13 @@
 # JOINER_OAUTH2_CLIENT_SECRET=
 # JOINER_GUILD_ID=
 # JOINER_FAILED_JOIN_WEBHOOK_URL=
+
+# The following environment variables are used when using the 'datadog' profile:
+
+# Required:
+# DD_API_KEY=
+#
+# Optional:
+# DD_SITE=us5.datadoghq.com
+# DD_SERVICE=E6ng (Dev)
+# DD_ENV=local
diff --git a/Gemfile b/Gemfile
index 29d0d8b61..468a0c105 100644
--- a/Gemfile
+++ b/Gemfile
@@ -35,6 +35,8 @@ gem "rugged"
 # Blocked by unicorn which lacks a release with Rack 3 support
 gem "rack", "~> 2.0"
 
+gem "datadog", require: "datadog/auto_instrument"
+
 gem 'opensearch-ruby'
 
 gem 'mailgun-ruby'
diff --git a/Gemfile.lock b/Gemfile.lock
index d90902f2b..192d6bba1 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -115,7 +115,14 @@ GEM
       rexml
     crass (1.0.6)
     dalli (3.2.6)
+    datadog (2.0.0.beta1)
+      base64
+      debase-ruby_core_source (= 3.3.1)
+      libdatadog (~> 6.0.0.2.0)
+      libddwaf (~> 1.14.0.0.0)
+      msgpack
     date (3.3.4)
+    debase-ruby_core_source (3.3.1)
     debug (1.9.1)
       irb (~> 1.10)
       reline (>= 0.3.8)
@@ -163,6 +170,9 @@ GEM
     jsonapi-renderer (0.2.2)
     kgio (2.11.4)
     language_server-protocol (3.17.0.3)
+    libdatadog (6.0.0.2.0)
+    libddwaf (1.14.0.0.0)
+      ffi (~> 1.0)
     listen (3.8.0)
       rb-fsevent (~> 0.10, >= 0.10.3)
       rb-inotify (~> 0.9, >= 0.9.10)
@@ -380,6 +390,7 @@ DEPENDENCIES
   bcrypt
   bootsnap
   dalli
+  datadog
   debug
   diffy
   dotenv
diff --git a/app/logical/danbooru_logger.rb b/app/logical/danbooru_logger.rb
index 4ce6e740b..9fc69e843 100644
--- a/app/logical/danbooru_logger.rb
+++ b/app/logical/danbooru_logger.rb
@@ -1,20 +1,22 @@
 # frozen_string_literal: true
 
 class DanbooruLogger
-  def self.log(exception, expected: false, **_params)
+  def self.log(exception, expected: false)
     if expected
       Rails.logger.info("#{exception.class}: #{exception.message}")
     else
       backtrace = Rails.backtrace_cleaner.clean(exception.backtrace).join("\n")
       Rails.logger.error("#{exception.class}: #{exception.message}\n#{backtrace}")
     end
+
+    Datadog::Tracing.active_span&.set_error(exception) unless expected
   end
 
   def self.initialize(user)
-    add_attributes("user.id" => user.id, "user.name" => user.name)
+    add_attributes("user.id" => user.id) unless user.is_anonymous?
   end
 
   def self.add_attributes(**)
-    # noop
+    Datadog::Tracing.active_span&.set_tags(**)
   end
 end
diff --git a/app/models/application_record.rb b/app/models/application_record.rb
index 091dd5f5c..cfdefcd19 100644
--- a/app/models/application_record.rb
+++ b/app/models/application_record.rb
@@ -217,8 +217,7 @@ class ApplicationRecord < ActiveRecord::Base
       def with_timeout(n, default_value = nil)
         connection.execute("SET STATEMENT_TIMEOUT = #{n}") unless Rails.env == "test"
         yield
-      rescue ::ActiveRecord::StatementInvalid => x
-        DanbooruLogger.log(x, expected: true)
+      rescue ::ActiveRecord::StatementInvalid
         return default_value
       ensure
         connection.execute("SET STATEMENT_TIMEOUT = #{CurrentUser.user.try(:statement_timeout) || 3_000}") unless Rails.env == "test"
diff --git a/app/models/tag_alias.rb b/app/models/tag_alias.rb
index 67e9cfc26..f4b112099 100644
--- a/app/models/tag_alias.rb
+++ b/app/models/tag_alias.rb
@@ -206,8 +206,6 @@ class TagAlias < TagRelationship
         forum_updater.update(failure_message(e), "FAILED") if update_topic
         update_columns(status: "error: #{e}")
       end
-
-      DanbooruLogger.log(e, tag_alias_id: id, antecedent_name: antecedent_name, consequent_name: consequent_name)
     end
   end
 
diff --git a/app/models/tag_implication.rb b/app/models/tag_implication.rb
index 9c74539f8..444992cc3 100644
--- a/app/models/tag_implication.rb
+++ b/app/models/tag_implication.rb
@@ -138,8 +138,6 @@ class TagImplication < TagRelationship
 
         forum_updater.update(failure_message(e), "FAILED") if update_topic
         update_columns(status: "error: #{e}")
-
-        DanbooruLogger.log(e, tag_implication_id: id, antecedent_name: antecedent_name, consequent_name: consequent_name)
       end
     end
 
diff --git a/config/initializers/01_sensitive_params.rb b/config/initializers/01_sensitive_params.rb
new file mode 100644
index 000000000..30944b7f3
--- /dev/null
+++ b/config/initializers/01_sensitive_params.rb
@@ -0,0 +1,10 @@
+# frozen_string_literal: true
+
+module SensitiveParams
+  # Common values for Rails and Datadog query parameter filtering
+  PARAMS = %i[passw secret token _key crypt salt certificate otp ssn email].freeze
+
+  def self.to_datadog_regex
+    Regexp.new("(?:#{PARAMS.join('|')})[^&]*=[^&]*")
+  end
+end
diff --git a/config/initializers/datadog.rb b/config/initializers/datadog.rb
new file mode 100644
index 000000000..40a465a57
--- /dev/null
+++ b/config/initializers/datadog.rb
@@ -0,0 +1,14 @@
+# frozen_string_literal: true
+
+Datadog.configure do |c|
+  c.tracing.enabled = !Rails.env.test? && ENV["DD_API_KEY"].present?
+  c.logger.level = Logger::WARN
+
+  c.tracing.instrument :rack, quantize: {
+    query: {
+      obfuscate: {
+        regex: SensitiveParams.to_datadog_regex,
+      },
+    },
+  }
+end
diff --git a/config/initializers/filter_parameter_logging.rb b/config/initializers/filter_parameter_logging.rb
index f11e977cc..161cca8b1 100644
--- a/config/initializers/filter_parameter_logging.rb
+++ b/config/initializers/filter_parameter_logging.rb
@@ -5,6 +5,4 @@
 # Configure parameters to be partially matched (e.g. passw matches password) and filtered from the log file.
 # Use this to limit dissemination of sensitive information.
 # See the ActiveSupport::ParameterFilter documentation for supported notations and behaviors.
-Rails.application.config.filter_parameters += [
-  :passw, :secret, :token, :_key, :crypt, :salt, :certificate, :otp, :ssn, :email
-]
+Rails.application.config.filter_parameters += SensitiveParams::PARAMS
diff --git a/docker-compose.yml b/docker-compose.yml
index 29ce2a8e8..8dc62b9e1 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -15,6 +15,7 @@ x-environment: &common-env
   SESSION_SECRET_KEY: 44b4f44e9f253c406cbe727d403d500c1cecff943e4d2aea8f5447f28846fffe
   # Hide annoying output from libvips on corrupt files
   VIPS_WARNING: "0"
+  DD_TRACE_STARTUP_LOGS: false
 
 x-depends-on: &common-depends-on
   opensearch:
@@ -43,6 +44,9 @@ services:
     environment:
       <<: *common-env
       RAILS_ENV: development
+      DD_AGENT_HOST: datadog-agent
+      DD_SERVICE: ${DD_SERVICE:-}
+      DD_ENV: ${DD_ENV:-}
     depends_on:
       <<: *common-depends-on
       autocompleted:
@@ -118,6 +122,17 @@ services:
     command: iqdb http 0.0.0.0 5588 /iqdb/e621_v2.db
     volumes:
       - iqdb_data:/iqdb
+  
+  datadog-agent:
+    image: datadog/agent:7.52.0
+    environment:
+      DD_API_KEY: ${DD_API_KEY:-}
+      DD_SITE: ${DD_SITE:-us5.datadoghq.com}
+      DD_HOSTNAME: datadog-agent
+      DD_LOG_LEVEL: WARN
+      DD_APM_NON_LOCAL_TRAFFIC: true
+    profiles:
+      - datadog
 
   # Discord integration
 
diff --git a/test/unit/datadog_test.rb b/test/unit/datadog_test.rb
new file mode 100644
index 000000000..9afba546f
--- /dev/null
+++ b/test/unit/datadog_test.rb
@@ -0,0 +1,25 @@
+# frozen_string_literal: true
+
+require "test_helper"
+
+class DatadogTest < ActiveSupport::TestCase
+  def assert_match_group(expected, query)
+    assert_equal(expected, query[SensitiveParams.to_datadog_regex])
+  end
+
+  def assert_no_match_group(query)
+    assert_nil(query[SensitiveParams.to_datadog_regex])
+  end
+
+  should "filters query parameters" do
+    assert_match_group("password=hunter2", "password=hunter2")
+    assert_match_group("password=hunter2", "?abc=def&password=hunter2&foo=bar")
+    # These partial matches are fine, just don't let datadog grab it
+    assert_match_group("password]=hunter2", "?abc=def&user[password]=hunter2&foo=bar")
+    assert_match_group("password=hunter2", "old_password=hunter2")
+    assert_match_group("password_old=hunter2", "password_old=hunter2")
+
+    assert_no_match_group("something=else")
+    assert_no_match_group("search[foo]=bar")
+  end
+end