diff --git a/app/services/evss_claim_service.rb b/app/services/evss_claim_service.rb
index 0c390668bd..366ec24996 100644
--- a/app/services/evss_claim_service.rb
+++ b/app/services/evss_claim_service.rb
@@ -53,7 +53,7 @@ def request_decision(claim)
   # upload file to s3 and enqueue job to upload to EVSS, used by Claim Status Tool
   # EVSS::DocumentsService is where the uploading of documents actually happens
   def upload_document(evss_claim_document)
-    uploader = EVSSClaimDocumentUploader.new(@user.uuid, evss_claim_document.uploader_ids)
+    uploader = EVSSClaimDocumentUploader.new(@user.user_account_uuid, evss_claim_document.uploader_ids)
     uploader.store!(evss_claim_document.file_obj)
 
     # the uploader sanitizes the filename before storing, so set our doc to match
@@ -63,7 +63,8 @@ def upload_document(evss_claim_document)
     headers = auth_headers.clone
     headers_supplemented = supplement_auth_headers(evss_claim_document.evss_claim_id, headers)
 
-    job_id = EVSS::DocumentUpload.perform_async(headers, @user.uuid, evss_claim_document.to_serializable_hash)
+    job_id = EVSS::DocumentUpload.perform_async(headers, @user.user_account_uuid,
+                                                evss_claim_document.to_serializable_hash)
 
     record_workaround('document_upload', evss_claim_document.evss_claim_id, job_id) if headers_supplemented
 
diff --git a/app/sidekiq/evss/document_upload.rb b/app/sidekiq/evss/document_upload.rb
index ca8475e3cb..36bc031130 100644
--- a/app/sidekiq/evss/document_upload.rb
+++ b/app/sidekiq/evss/document_upload.rb
@@ -8,6 +8,12 @@ class EVSS::DocumentUpload
   include Sidekiq::Job
   extend Logging::ThirdPartyTransaction::MethodWrapper
 
+  FILENAME_EXTENSION_MATCHER = /\.\w*$/
+  OBFUSCATED_CHARACTER_MATCHER = /[a-zA-Z\d]/
+
+  NOTIFY_SETTINGS = Settings.vanotify.services.benefits_management_tools
+  MAILER_TEMPLATE_ID = NOTIFY_SETTINGS.template_id.evidence_submission_failure_email
+
   attr_accessor :auth_headers, :user_uuid, :document_hash
 
   wrap_with_logging(
@@ -29,6 +35,31 @@ class EVSS::DocumentUpload
     rand(3600..3660) if count < 9
   end
 
+  sidekiq_retries_exhausted do |msg, _ex|
+    # There should be 3 args:
+    # 1) Auth headers needed to authenticate with EVSS
+    # 2) The uuid of the record in the UserAccount table
+    # 3) Document metadata
+
+    next unless Flipper.enabled?('cst_send_evidence_failure_emails')
+
+    icn = UserAccount.find(msg['args'][1]).icn
+    first_name = msg['args'].first['va_eauth_firstName'].titleize
+    filename = obscured_filename(msg['args'][2]['file_name'])
+    date_submitted = format_issue_instant_for_mailers(msg['created_at'])
+
+    notify_client.send_email(
+      recipient_identifier: { id_value: icn, id_type: 'ICN' },
+      template_id: MAILER_TEMPLATE_ID,
+      personalisation: { first_name:, filename:, date_submitted: }
+    )
+
+    ::Rails.logger.info('EVSS::DocumentUpload exhaustion handler email sent')
+  rescue => e
+    ::Rails.logger.error('EVSS::DocumentUpload exhaustion handler email error',
+                         { message: e.message })
+  end
+
   def perform(auth_headers, user_uuid, document_hash)
     @auth_headers = auth_headers
     @user_uuid = user_uuid
@@ -40,6 +71,33 @@ def perform(auth_headers, user_uuid, document_hash)
     clean_up!
   end
 
+  def self.obscured_filename(original_filename)
+    extension = original_filename[FILENAME_EXTENSION_MATCHER]
+    filename_without_extension = original_filename.gsub(FILENAME_EXTENSION_MATCHER, '')
+
+    if filename_without_extension.length > 5
+      # Obfuscate with the letter 'X'; we cannot obfuscate with special characters such as an asterisk,
+      # as these filenames appear in VA Notify Mailers and their templating engine uses markdown.
+      # Therefore, special characters can be interpreted as markdown and introduce formatting issues in the mailer
+      obfuscated_portion = filename_without_extension[3..-3].gsub(OBFUSCATED_CHARACTER_MATCHER, 'X')
+      filename_without_extension[0..2] + obfuscated_portion + filename_without_extension[-2..] + extension
+    else
+      original_filename
+    end
+  end
+
+  def self.format_issue_instant_for_mailers(issue_instant)
+    # We want to return all times in EDT
+    timestamp = Time.at(issue_instant).in_time_zone('America/New_York')
+
+    # We display dates in mailers in the format "May 1, 2024 3:01 p.m. EDT"
+    timestamp.strftime('%B %-d, %Y %-l:%M %P %Z').sub(/([ap])m/, '\1.m.')
+  end
+
+  def self.notify_client
+    VaNotify::Service.new(NOTIFY_SETTINGS.api_key)
+  end
+
   private
 
   def validate_document!
diff --git a/config/settings.yml b/config/settings.yml
index 9f6f33c3fa..71a94e5b8f 100644
--- a/config/settings.yml
+++ b/config/settings.yml
@@ -1372,6 +1372,10 @@ vanotify:
         form526_document_upload_failure_notification_template_id: form526_document_upload_failure_notification_template_id
         form4142_upload_failure_notification_template_id: form4142_upload_failure_notification_template_id
         form0781_upload_failure_notification_template_id: form0781_upload_failure_notification_template_id
+    benefits_management_tools:
+      api_key: fake_secret
+      template_id:
+        evidence_submission_failure_email: fake_template_id
     ivc_champva:
       api_key: fake_secret
       template_id:
diff --git a/config/settings/test.yml b/config/settings/test.yml
index 6352a32d9f..956eff1f36 100644
--- a/config/settings/test.yml
+++ b/config/settings/test.yml
@@ -158,6 +158,10 @@ vanotify:
         claim_submission_duplicate_text: oh_fake_duplicate_template_id
         claim_submission_timeout_text: oh_fake_timeout_template_id
         claim_submission_error_text: oh_fake_error_template_id
+    benefits_management_tools:
+      api_key: fake_secret
+      template_id:
+        evidence_submission_failure_email: fake_template_id
 
 res:
   base_url: https://fake_url.com
diff --git a/spec/sidekiq/evss/document_upload_spec.rb b/spec/sidekiq/evss/document_upload_spec.rb
index 98732c3ae0..42f124ee7f 100644
--- a/spec/sidekiq/evss/document_upload_spec.rb
+++ b/spec/sidekiq/evss/document_upload_spec.rb
@@ -5,8 +5,14 @@
 require 'evss/document_upload'
 
 RSpec.describe EVSS::DocumentUpload, type: :job do
+  subject { described_class }
+
   let(:client_stub) { instance_double('EVSS::DocumentsService') }
+  let(:notify_client_stub) { instance_double('VaNotify::Sidekiq') }
   let(:uploader_stub) { instance_double('EVSSClaimDocumentUploader') }
+
+  let(:user_account) { create(:user_account) }
+  let(:user_account_uuid) { user_account.id }
   let(:user) { FactoryBot.create(:user, :loa3) }
   let(:filename) { 'doctors-note.pdf' }
   let(:document_data) do
@@ -19,6 +25,18 @@
   end
   let(:auth_headers) { EVSS::AuthHeaders.new(user).to_h }
 
+  let(:issue_instant) { Time.now.to_i }
+  let(:args) do
+    {
+      'args' => [{ 'va_eauth_firstName' => 'Bob' }, user_account_uuid, { 'file_name' => filename }],
+      'created_at' => issue_instant
+    }
+  end
+
+  before do
+    allow(Rails.logger).to receive(:info)
+  end
+
   it 'retrieves the file and uploads to EVSS' do
     allow(EVSSClaimDocumentUploader).to receive(:new) { uploader_stub }
     allow(EVSS::DocumentsService).to receive(:new) { client_stub }
@@ -29,4 +47,56 @@
     expect(client_stub).to receive(:upload).with(file, document_data)
     described_class.new.perform(auth_headers, user.uuid, document_data.to_serializable_hash)
   end
+
+  context 'when cst_send_evidence_failure_emails is enabled' do
+    before do
+      Flipper.enable(:cst_send_evidence_failure_emails)
+    end
+
+    let(:formatted_submit_date) do
+      # We want to return all times in EDT
+      timestamp = Time.at(issue_instant).in_time_zone('America/New_York')
+
+      # We display dates in mailers in the format "May 1, 2024 3:01 p.m. EDT"
+      timestamp.strftime('%B %-d, %Y %-l:%M %P %Z').sub(/([ap])m/, '\1.m.')
+    end
+
+    it 'enqueues a failure notification mailer to send to the veteran' do
+      allow(VaNotify::Service).to receive(:new) { notify_client_stub }
+
+      subject.within_sidekiq_retries_exhausted_block(args) do
+        expect(notify_client_stub).to receive(:send_email).with(
+          {
+            recipient_identifier: { id_value: user_account.icn, id_type: 'ICN' },
+            template_id: 'fake_template_id',
+            personalisation: {
+              first_name: 'Bob',
+              filename: 'docXXXX-XXte.pdf',
+              date_submitted: formatted_submit_date
+            }
+          }
+        )
+
+        expect(Rails.logger)
+          .to receive(:info)
+          .with('EVSS::DocumentUpload exhaustion handler email sent')
+      end
+    end
+  end
+
+  context 'when cst_send_evidence_failure_emails is disabled' do
+    before do
+      Flipper.disable(:cst_send_evidence_failure_emails)
+    end
+
+    let(:issue_instant) { Time.now.to_i }
+
+    it 'does not enqueue a failure notification mailer to send to the veteran' do
+      allow(VaNotify::Service).to receive(:new) { notify_client_stub }
+
+      subject.within_sidekiq_retries_exhausted_block(args) do
+        expect(notify_client_stub).not_to receive(:send_email)
+      end
+    end
+  end
 end