diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index 32ae6be552c..cf7c5f8a517 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -2432,6 +2432,7 @@ en:
       search_tokenize_chinese_enabled: "You must disable 'search_tokenize_chinese' before enabling this setting."
       search_tokenize_japanese_enabled: "You must disable 'search_tokenize_japanese' before enabling this setting."
       discourse_connect_cannot_be_enabled_if_second_factor_enforced: "You cannot enable DiscourseConnect if 2FA is enforced."
+      delete_rejected_email_after_days: "This setting cannot be set lower than the delete_email_logs_after_days setting or greater than %{max}"
 
     placeholder:
       discourse_connect_provider_secrets:
diff --git a/config/site_settings.yml b/config/site_settings.yml
index 5f05a26a650..293edff401b 100644
--- a/config/site_settings.yml
+++ b/config/site_settings.yml
@@ -1266,7 +1266,7 @@ email:
   raw_rejected_email_max_length: 4000
   delete_rejected_email_after_days:
     default: 90
-    max: 36500
+    validator: "DeleteRejectedEmailAfterDaysValidator"
   enable_secondary_emails:
     client: true
     default: true
diff --git a/db/migrate/20220726164831_fix_delete_rejected_email_after_days_site_setting.rb b/db/migrate/20220726164831_fix_delete_rejected_email_after_days_site_setting.rb
new file mode 100644
index 00000000000..89ce57c1d8c
--- /dev/null
+++ b/db/migrate/20220726164831_fix_delete_rejected_email_after_days_site_setting.rb
@@ -0,0 +1,26 @@
+# frozen_string_literal: true
+class FixDeleteRejectedEmailAfterDaysSiteSetting < ActiveRecord::Migration[6.1]
+  def up
+    delete_rejected_email_after_days = DB.query_single("SELECT value FROM site_settings WHERE name = 'delete_rejected_email_after_days'").first
+    delete_email_logs_after_days = DB.query_single("SELECT value FROM site_settings WHERE name = 'delete_email_logs_after_days'").first
+
+    # These settings via the sql query return nil if they are using their default values
+    unless delete_email_logs_after_days
+      delete_email_logs_after_days = DeleteRejectedEmailAfterDaysValidator::MAX
+    end
+
+    # Only update if the setting is not using the default and it is lower than 'delete_email_logs_after_days'
+    if delete_rejected_email_after_days != nil && delete_rejected_email_after_days.to_i < delete_email_logs_after_days.to_i
+      execute <<~SQL
+      UPDATE site_settings
+      SET value = #{delete_email_logs_after_days.to_i}
+      WHERE name = 'delete_rejected_email_after_days'
+      SQL
+    end
+
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end
diff --git a/lib/validators/delete_rejected_email_after_days_validator.rb b/lib/validators/delete_rejected_email_after_days_validator.rb
new file mode 100644
index 00000000000..0ad322e7064
--- /dev/null
+++ b/lib/validators/delete_rejected_email_after_days_validator.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+class DeleteRejectedEmailAfterDaysValidator
+  MAX = 36500
+
+  def initialize(opts = {})
+    @opts = opts
+  end
+
+  def valid_value?(value)
+    @valid = value.to_i >= SiteSetting.delete_email_logs_after_days && value.to_i <= MAX
+  end
+
+  def error_message
+    I18n.t("site_settings.errors.delete_rejected_email_after_days", max: MAX) if !@valid
+  end
+end
diff --git a/spec/lib/validators/delete_rejected_email_after_days_spec.rb b/spec/lib/validators/delete_rejected_email_after_days_spec.rb
new file mode 100644
index 00000000000..4a410983ad3
--- /dev/null
+++ b/spec/lib/validators/delete_rejected_email_after_days_spec.rb
@@ -0,0 +1,15 @@
+# frozen_string_literal: true
+
+describe DeleteRejectedEmailAfterDaysValidator do
+
+  it 'is not valid if value is smaller than the value of SiteSetting.delete_email_logs_after_days' do
+    SiteSetting.delete_email_logs_after_days = 90
+
+    expect { SiteSetting.delete_rejected_email_after_days = 89 }.to raise_error(Discourse::InvalidParameters)
+  end
+
+  it "is not valid if value is greater than #{DeleteRejectedEmailAfterDaysValidator::MAX}" do
+    expect { SiteSetting.delete_rejected_email_after_days = DeleteRejectedEmailAfterDaysValidator::MAX + 1 }.to raise_error(Discourse::InvalidParameters)
+  end
+
+end