diff --git a/app/jobs/contract/human_follow_up_job.rb b/app/jobs/contract/human_follow_up_job.rb
new file mode 100644
index 0000000000..4dc005af5e
--- /dev/null
+++ b/app/jobs/contract/human_follow_up_job.rb
@@ -0,0 +1,19 @@
+# frozen_string_literal: true
+
+class Contract
+  # Nudges HCB's party when an agreement they're the point of contact for is
+  # still unsigned. Unlike Contract::Party::ReminderJob this doesn't care
+  # whether HCB is the one holding things up (or maybe they forgot to sign...).
+  class HumanFollowUpJob < ApplicationJob
+    queue_as :low
+    discard_on ActiveJob::DeserializationError
+
+    def perform(contract)
+      return unless contract.sent?
+
+      ContractMailer.with(contract:).human_follow_up.deliver_later
+    end
+
+  end
+
+end
diff --git a/app/mailers/contract_mailer.rb b/app/mailers/contract_mailer.rb
new file mode 100644
index 0000000000..ef7be8dec5
--- /dev/null
+++ b/app/mailers/contract_mailer.rb
@@ -0,0 +1,13 @@
+# frozen_string_literal: true
+
+class ContractMailer < ApplicationMailer
+  before_action { @contract = params[:contract] }
+
+  def human_follow_up
+    @party = @contract.party(:hcb)
+    return if @party.nil?
+
+    mail to: @party.email, subject: @contract.human_follow_up_email_subject
+  end
+
+end
diff --git a/app/models/contract.rb b/app/models/contract.rb
index db1eddea0d..8c7526e20a 100644
--- a/app/models/contract.rb
+++ b/app/models/contract.rb
@@ -185,6 +185,10 @@ def agreement_name
     "agreement"
   end
 
+  def human_follow_up_email_subject
+    "[Update] #{event_name}'s #{agreement_name} still isn't signed 📝"
+  end
+
   def redirect_path
     contractable.contract_redirect_path
   end
diff --git a/app/models/contract/fiscal_sponsorship.rb b/app/models/contract/fiscal_sponsorship.rb
index a0f6d59a99..4434e72a35 100644
--- a/app/models/contract/fiscal_sponsorship.rb
+++ b/app/models/contract/fiscal_sponsorship.rb
@@ -36,7 +36,10 @@
 
 class Contract
   class FiscalSponsorship < Contract
+    HUMAN_FOLLOW_UP_AFTER = 1.month
+
     after_update_commit :create_document!, if: ->{ event.present? && sent_with_docuseal? && aasm_state_previously_changed?(to: "signed") }
+    after_update_commit :schedule_human_follow_up, if: ->{ aasm_state_previously_changed?(to: "sent") }
 
     def payload
       signee = party :signee
@@ -138,6 +141,10 @@ def agreement_name
       "fiscal sponsorship agreement"
     end
 
+    def schedule_human_follow_up
+      Contract::HumanFollowUpJob.set(wait: HUMAN_FOLLOW_UP_AFTER).perform_later(self)
+    end
+
     def required_roles
       ["hcb", "signee"]
     end
diff --git a/app/tasks/maintenance/schedule_contract_human_follow_ups_task.rb b/app/tasks/maintenance/schedule_contract_human_follow_ups_task.rb
new file mode 100644
index 0000000000..06c0f1cda6
--- /dev/null
+++ b/app/tasks/maintenance/schedule_contract_human_follow_ups_task.rb
@@ -0,0 +1,20 @@
+# frozen_string_literal: true
+
+module Maintenance
+  class ScheduleContractHumanFollowUpsTask < MaintenanceTasks::Task
+    def collection
+      Contract::FiscalSponsorship.where(aasm_state: :sent)
+    end
+
+    def process(contract)
+      due_at = contract.created_at + Contract::FiscalSponsorship::HUMAN_FOLLOW_UP_AFTER
+
+      if due_at.future?
+        Contract::HumanFollowUpJob.set(wait_until: due_at).perform_later(contract)
+      else
+        Contract::HumanFollowUpJob.perform_later(contract)
+      end
+    end
+
+  end
+end
diff --git a/app/views/contract_mailer/human_follow_up.html.erb b/app/views/contract_mailer/human_follow_up.html.erb
new file mode 100644
index 0000000000..ed05a478fb
--- /dev/null
+++ b/app/views/contract_mailer/human_follow_up.html.erb
@@ -0,0 +1,46 @@
+<p>Hi there! 👋</p>
+
+<p>
+  The <%= @contract.agreement_name %> for
+  <% if @contract.contractable.is_a?(Event::Application) %>
+    <%= link_to "#{@contract.event_name}'s application", submission_application_url(@contract.contractable) %>
+  <% elsif @contract.contractable.is_a?(OrganizerPositionInvite) %>
+    <%= link_to "an invitation to #{@contract.event_name}", organizer_position_invite_url(@contract.contractable) %>
+  <% else %>
+    <%= @contract.event_name %>
+  <% end %>
+  was sent <%= time_ago_in_words @contract.created_at %> ago and still hasn't been signed by everyone.
+  You're the HCB point of contact on it, so we wanted to give you an update.
+</p>
+
+<p>Still waiting on:</p>
+
+<ul>
+  <% @contract.parties.reject(&:signed?).each do |pending_party| %>
+    <li>
+      <%= pending_party.hcb? ? "You (HCB Operations)" : pending_party.role.humanize %> &mdash;
+      <%= pending_party.email %>
+    </li>
+  <% end %>
+</ul>
+
+<% if @party.pending? %>
+  <p>
+    <%= link_to "Click here", contract_party_url(@party) %> to sign your part of the agreement.
+  </p>
+<% end %>
+
+<% if @contract.external_id.present? %>
+  <p>
+    <%= link_to "View the submission on DocuSeal", @contract.docuseal_submission_url %> to see where it's stuck.
+  </p>
+<% end %>
+
+<p>
+  If this agreement is no longer needed, you can void it so it stops chasing everyone for signatures.
+</p>
+
+<p>
+  Thanks!<br>
+  Here's a cookie 🍪
+</p>