diff --git a/app/jobs/salesforce/role_sync_job.rb b/app/jobs/salesforce/role_sync_job.rb
index 2465ad9db..9663b4ac4 100644
--- a/app/jobs/salesforce/role_sync_job.rb
+++ b/app/jobs/salesforce/role_sync_job.rb
@@ -18,6 +18,15 @@ def perform(role_id:)
 
       return if role.student?
 
+      # The Contact_Editor_Affiliation__c row uses Salesforce external-ID lookups to resolve
+      # its parent Editor__c (school) and Contact (user). If either parent has not yet been
+      # pushed to Salesforce, Heroku Connect rejects the INSERT permanently with a
+      # "Foreign key external ID ... not found" error and the row is stuck FAILED in the
+      # mirror. Raising SalesforceRecordNotFound here defers the affiliation write via the
+      # SalesforceSyncJob retry_on, giving the parent records time to land in Salesforce.
+      ensure_parent_synced!(Salesforce::School, :editoruuid__c, role.school_id, 'Editor__c')
+      ensure_parent_synced!(Salesforce::Contact, :pi_accounts_unique_id__c, role.user_id, 'Contact')
+
       sf_role = Salesforce::Role.find_or_initialize_by(affiliation_id__c: role_id)
       sf_role.attributes = sf_role_attributes(role:)
 
@@ -32,6 +41,13 @@ def perform(role_id:)
 
     private
 
+    def ensure_parent_synced!(model, external_id_field, external_id, label)
+      return if model.where(external_id_field => external_id).where.not(sfid: nil).exists?
+
+      raise SalesforceRecordNotFound,
+            "#{label} not yet synced for #{external_id_field}: #{external_id}"
+    end
+
     def sf_role_attributes(role:)
       mapped_attributes(role:).to_h do |sf_field, value|
         value = truncate_value(sf_field:, value:) if value.is_a?(String)
diff --git a/spec/jobs/salesforce/role_sync_job_spec.rb b/spec/jobs/salesforce/role_sync_job_spec.rb
index 2f77bd98e..2df328a3b 100644
--- a/spec/jobs/salesforce/role_sync_job_spec.rb
+++ b/spec/jobs/salesforce/role_sync_job_spec.rb
@@ -6,6 +6,12 @@
   subject(:perform_job) { described_class.perform_now(role_id: role.id) }
 
   let(:role) { create(:role) }
+  let!(:sf_school) do
+    create(:salesforce_school, editoruuid__c: role.school_id, sfid: SecureRandom.alphanumeric(18))
+  end
+  let!(:sf_contact) do
+    create(:salesforce_contact, pi_accounts_unique_id__c: role.user_id, sfid: SecureRandom.alphanumeric(18))
+  end
 
   around do |example|
     ClimateControl.modify(SALESFORCE_ENABLED: 'true') { example.run }
@@ -53,6 +59,58 @@
     end
   end
 
+  context 'when the parent Editor__c is not yet synced to Salesforce' do
+    before { sf_school.update!(sfid: nil) }
+
+    it 'retries the job to defer the affiliation write' do
+      expect { perform_job }.to have_enqueued_job(described_class).with(role_id: role.id)
+    end
+
+    it 'does not write the affiliation to the mirror' do
+      perform_job
+      expect(Salesforce::Role.find_by(affiliation_id__c: role.id)).to be_nil
+    end
+  end
+
+  context 'when there is no Salesforce::School row for the role school' do
+    before { sf_school.destroy }
+
+    it 'retries the job' do
+      expect { perform_job }.to have_enqueued_job(described_class).with(role_id: role.id)
+    end
+
+    it 'does not write the affiliation to the mirror' do
+      perform_job
+      expect(Salesforce::Role.find_by(affiliation_id__c: role.id)).to be_nil
+    end
+  end
+
+  context 'when the parent Contact is not yet synced to Salesforce' do
+    before { sf_contact.update!(sfid: nil) }
+
+    it 'retries the job to defer the affiliation write' do
+      expect { perform_job }.to have_enqueued_job(described_class).with(role_id: role.id)
+    end
+
+    it 'does not write the affiliation to the mirror' do
+      perform_job
+      expect(Salesforce::Role.find_by(affiliation_id__c: role.id)).to be_nil
+    end
+  end
+
+  context 'when there is no Salesforce::Contact row for the role user' do
+    before { sf_contact.destroy }
+
+    it 'retries the job' do
+      expect { perform_job }.to have_enqueued_job(described_class).with(role_id: role.id)
+    end
+
+    it 'does not write the affiliation to the mirror' do
+      perform_job
+      expect(Salesforce::Role.find_by(affiliation_id__c: role.id)).to be_nil
+    end
+  end
+
   context 'when SALESFORCE_ENABLED is false' do
     around do |example|
       ClimateControl.modify(SALESFORCE_ENABLED: 'false') do