diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index 6b109224397..5533e39c4f6 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -188,9 +188,35 @@ def service_provider_mfa_setup_url
     service_provider_mfa_policy.user_needs_sp_auth_method_setup? ? two_factor_options_url : nil
   end
 
+  def fix_broken_personal_key_url
+    return if !current_user.broken_personal_key?
+
+    flash[:info] = t('account.personal_key.needs_new')
+
+    pii_unlocked = user_session[:decrypted_pii].present?
+
+    if pii_unlocked
+      cacher = Pii::Cacher.new(current_user, user_session)
+      profile = current_user.active_profile
+      user_session[:personal_key] = profile.encrypt_recovery_pii(cacher.fetch)
+      profile.save!
+
+      analytics.track_event(Analytics::BROKEN_PERSONAL_KEY_REGENERATED)
+
+      manage_personal_key_url
+    else
+      user_session[:needs_new_personal_key] = true
+
+      capture_password_url
+    end
+  end
+
   def after_sign_in_path_for(_user)
-    service_provider_mfa_setup_url || add_piv_cac_setup_url ||
-      user_session.delete(:stored_location) || sp_session_request_url_with_updated_params ||
+    service_provider_mfa_setup_url ||
+      add_piv_cac_setup_url ||
+      fix_broken_personal_key_url ||
+      user_session.delete(:stored_location) ||
+      sp_session_request_url_with_updated_params ||
       signed_in_url
   end
 
diff --git a/app/controllers/password_capture_controller.rb b/app/controllers/password_capture_controller.rb
index 322ffa1dd85..94dd31ad2a8 100644
--- a/app/controllers/password_capture_controller.rb
+++ b/app/controllers/password_capture_controller.rb
@@ -6,12 +6,15 @@ class PasswordCaptureController < ApplicationController
   before_action :confirm_two_factor_authenticated
   before_action :apply_secure_headers_override
 
+  helper_method :password_header
+
   def new
     session[:password_attempts] ||= 0
   end
 
   def create
     if current_user.valid_password?(password)
+      user_session.delete(:needs_new_personal_key)
       handle_valid_password
     else
       handle_invalid_password
@@ -20,6 +23,14 @@ def create
 
   private
 
+  def password_header
+    if user_session[:needs_new_personal_key]
+      t('headings.passwords.confirm_for_personal_key')
+    else
+      t('headings.passwords.confirm')
+    end
+  end
+
   def password
     params.require(:user)[:password]
   end
diff --git a/app/models/user.rb b/app/models/user.rb
index 5260b7d00f4..1253749639c 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -101,6 +101,16 @@ def default_phone_configuration
     phone_configurations.order('made_default_at DESC NULLS LAST, created_at').first
   end
 
+  def broken_personal_key?
+    window_start = IdentityConfig.store.broken_personal_key_window_start
+    window_finish = IdentityConfig.store.broken_personal_key_window_finish
+    last_personal_key_at = self.encrypted_recovery_code_digest_generated_at
+
+    (!last_personal_key_at || last_personal_key_at < window_finish) &&
+      active_profile.present? &&
+      (window_start..window_finish).cover?(active_profile.verified_at)
+  end
+
   # To send emails asynchronously via ActiveJob.
   def send_devise_notification(notification, *args)
     devise_mailer.send(notification, self, *args).deliver_now_or_later
diff --git a/app/services/analytics.rb b/app/services/analytics.rb
index de21ddd52d8..ee34273cd70 100644
--- a/app/services/analytics.rb
+++ b/app/services/analytics.rb
@@ -135,6 +135,7 @@ def browser_attributes
   AUTHENTICATION_CONFIRMATION_RESET = 'Authentication Confirmation: Reset selected'
   BANNED_USER_REDIRECT = 'Banned User redirected'
   BANNED_USER_VISITED = 'Banned User visited'
+  BROKEN_PERSONAL_KEY_REGENERATED = 'Broken Personal Key: Regenerated'
   DOC_AUTH = 'Doc Auth' # visited or submitted is appended
   DOC_AUTH_ASYNC = 'Doc Auth Async'
   DOC_AUTH_WARNING = 'Doc Auth Warning'
diff --git a/app/views/password_capture/new.html.erb b/app/views/password_capture/new.html.erb
index 605eb70f5d2..bb8a35d9819 100644
--- a/app/views/password_capture/new.html.erb
+++ b/app/views/password_capture/new.html.erb
@@ -1,6 +1,6 @@
 <% title t('titles.visitors.index') %>
 
-<%= render PageHeadingComponent.new.with_content(t('headings.passwords.confirm')) %>
+<%= render PageHeadingComponent.new.with_content(password_header) %>
 
 <%= validated_form_for(
       current_user,
diff --git a/config/application.yml.default b/config/application.yml.default
index fdbd2ecbf59..27fc1c6d4cb 100644
--- a/config/application.yml.default
+++ b/config/application.yml.default
@@ -50,6 +50,8 @@ aws_logo_bucket: ''
 aws_region: 'us-west-2'
 aws_kms_multi_region_enabled: false
 backup_code_cost: '2000$8$1$'
+broken_personal_key_window_start: '2021-07-29T00:00:00Z'
+broken_personal_key_window_finish: '2021-09-22T00:00:00Z'
 country_phone_number_overrides: '{}'
 doc_auth_error_dpi_threshold: 290
 doc_auth_error_sharpness_threshold: 40
diff --git a/config/locales/account/en.yml b/config/locales/account/en.yml
index f02c5b60ae2..014266d1d3c 100644
--- a/config/locales/account/en.yml
+++ b/config/locales/account/en.yml
@@ -107,6 +107,8 @@ en:
       get_new_description: When you receive a new personal key, your old personal key
         will not work anymore.
       last_generated: 'Last generated on %{timestamp}'
+      needs_new: Your account needs a new personal key. Your old personal key will not
+        work if you forget your password.
       old_key_will_not_work: Please print, copy, or download the new personal key
         below. Your old personal key will not work if you forget your password.
       reset_instructions: Reset your personal key if you don’t have it. You’ll need
diff --git a/config/locales/account/es.yml b/config/locales/account/es.yml
index 023c8460d7c..274de96f553 100644
--- a/config/locales/account/es.yml
+++ b/config/locales/account/es.yml
@@ -107,6 +107,8 @@ es:
       get_new: Obtenga una nueva clave personal
       get_new_description: Su antigua clave personal dejará de funcionar en cuanto reciba una nueva.
       last_generated: 'Generada por última vez en %{timestamp}'
+      needs_new: Se requiere una nueva clave personal para su cuenta. Su antigua clave
+        personal no funcionará si se olvida de su contraseña.
       old_key_will_not_work: Por favor, imprima, copie o descargue la nueva clave
         personal que aparece a continuación. Su antigua clave personal no
         funcionará si olvida su contraseña.
diff --git a/config/locales/account/fr.yml b/config/locales/account/fr.yml
index fc65acfaa26..8af0daf971a 100644
--- a/config/locales/account/fr.yml
+++ b/config/locales/account/fr.yml
@@ -114,6 +114,8 @@ fr:
       get_new_description: Lorsque vous recevez une nouvelle clé personnelle, votre
         ancienne clé personnelle ne fonctionnera plus.
       last_generated: 'Dernière génération le %{timestamp}'
+      needs_new: Votre compte a besoin d’une nouvelle clé personnelle. Votre ancienne
+        clé personnelle ne fonctionnera pas si vous oubliez votre mot de passe.
       old_key_will_not_work: Veuillez imprimer, copier ou télécharger la nouvelle clé
         personnelle ci-dessous. Votre ancienne clé personnelle ne fonctionnera
         pas si vous oubliez votre mot de passe.
diff --git a/config/locales/headings/en.yml b/config/locales/headings/en.yml
index 29abfd443af..1746afd5dc8 100644
--- a/config/locales/headings/en.yml
+++ b/config/locales/headings/en.yml
@@ -32,6 +32,7 @@ en:
     passwords:
       change: Change your password
       confirm: Confirm your current password to continue
+      confirm_for_personal_key: Enter password and get a new personal key
       forgot: Forgot your password?
     personal_key: Save your personal key
     piv_cac:
diff --git a/config/locales/headings/es.yml b/config/locales/headings/es.yml
index 3f0d6e34932..6315c930147 100644
--- a/config/locales/headings/es.yml
+++ b/config/locales/headings/es.yml
@@ -32,6 +32,7 @@ es:
     passwords:
       change: Cambie su contraseña
       confirm: Confirme la contraseña actual para continuar
+      confirm_for_personal_key: Introduzca la contraseña y obtenga una nueva clave personal
       forgot: '¿Olvidó su contraseña?'
     personal_key: Guarda tu clave personal
     piv_cac:
diff --git a/config/locales/headings/fr.yml b/config/locales/headings/fr.yml
index 9416525f83e..c00f6e3cfb8 100644
--- a/config/locales/headings/fr.yml
+++ b/config/locales/headings/fr.yml
@@ -32,6 +32,7 @@ fr:
     passwords:
       change: Changez votre mot de passe
       confirm: Confirmez votre mot de passe actuel pour continuer
+      confirm_for_personal_key: Entrez le mot de passe et obtenez une nouvelle clé personnelle
       forgot: Vous avez oublié votre mot de passe?
     personal_key: Enregistrez votre clé personnelle
     piv_cac:
diff --git a/lib/identity_config.rb b/lib/identity_config.rb
index 7d3ccd10ab3..1a19f7e939f 100644
--- a/lib/identity_config.rb
+++ b/lib/identity_config.rb
@@ -107,6 +107,8 @@ def self.build_store(config_map)
     config.add(:aws_logo_bucket, type: :string)
     config.add(:aws_region, type: :string)
     config.add(:backup_code_cost, type: :string)
+    config.add(:broken_personal_key_window_start, type: :timestamp)
+    config.add(:broken_personal_key_window_finish, type: :timestamp)
     config.add(:country_phone_number_overrides, type: :json)
     config.add(:dashboard_api_token, type: :string)
     config.add(:dashboard_url, type: :string)
diff --git a/spec/features/users/sign_in_spec.rb b/spec/features/users/sign_in_spec.rb
index a913788f081..797c7b32f34 100644
--- a/spec/features/users/sign_in_spec.rb
+++ b/spec/features/users/sign_in_spec.rb
@@ -664,6 +664,11 @@
   it_behaves_like 'signing in with wrong credentials', :saml
   it_behaves_like 'signing in with wrong credentials', :oidc
 
+  it_behaves_like 'signing in as proofed account with broken personal key', :saml, sp_ial: 1
+  it_behaves_like 'signing in as proofed account with broken personal key', :oidc, sp_ial: 1
+  it_behaves_like 'signing in as proofed account with broken personal key', :saml, sp_ial: 2
+  it_behaves_like 'signing in as proofed account with broken personal key', :oidc, sp_ial: 2
+
   context 'user signs in and chooses another authentication method' do
     it 'signs out the user if they choose to cancel' do
       user = create(:user, :signed_up)
diff --git a/spec/models/user_spec.rb b/spec/models/user_spec.rb
index c5a993e987c..2a40a29100f 100644
--- a/spec/models/user_spec.rb
+++ b/spec/models/user_spec.rb
@@ -411,4 +411,86 @@
       end
     end
   end
+
+  describe '#broken_personal_key?' do
+    before do
+      allow(IdentityConfig.store).to receive(:broken_personal_key_window_start).
+        and_return(3.days.ago)
+      allow(IdentityConfig.store).to receive(:broken_personal_key_window_finish).
+        and_return(1.day.ago)
+    end
+
+    let(:user) { build(:user) }
+
+    context 'for a user with no profile' do
+      it { expect(user.broken_personal_key?).to eq(false) }
+    end
+
+    context 'for a user with a profile that is not verified' do
+      before do
+        create(:profile, user: user, activated_at: nil, verified_at: nil)
+      end
+
+      it { expect(user.broken_personal_key?).to eq(false) }
+    end
+
+    context 'for a user with a profile verified before the broken key window' do
+      before do
+        create(
+          :profile,
+          user: user,
+          active: true,
+          activated_at: 5.days.ago,
+          verified_at: 5.days.ago,
+        )
+      end
+
+      it { expect(user.broken_personal_key?).to eq(false) }
+    end
+
+    context 'for a user with a profile verified after the broken key window' do
+      before do
+        create(:profile, :active, :verified, user: user)
+      end
+
+      it { expect(user.broken_personal_key?).to eq(false) }
+    end
+
+    context 'for a user with a profile verified during the broken key window' do
+      let(:personal_key_generated_at) { nil }
+      let(:verified_at) { 2.days.ago }
+
+      let(:user) do
+        build(:user, encrypted_recovery_code_digest_generated_at: personal_key_generated_at)
+      end
+
+      before do
+        create(
+          :profile,
+          user: user,
+          active: true,
+          activated_at: verified_at,
+          verified_at: verified_at,
+        )
+      end
+
+      context 'for a user missing the personal key verified timestamp (legacy data)' do
+        let(:personal_key_generated_at) { nil }
+
+        it { expect(user.broken_personal_key?).to eq(true) }
+      end
+
+      context 'for a personal key generated before the window ends' do
+        let(:personal_key_generated_at) { 2.days.ago }
+
+        it { expect(user.broken_personal_key?).to eq(true) }
+      end
+
+      context 'for a personal key generated after the window (fixed)' do
+        let(:personal_key_generated_at) { Time.zone.now }
+
+        it { expect(user.broken_personal_key?).to eq(false) }
+      end
+    end
+  end
 end
diff --git a/spec/support/shared_examples/sign_in.rb b/spec/support/shared_examples/sign_in.rb
index 8b7b449bf29..4ecbf52561b 100644
--- a/spec/support/shared_examples/sign_in.rb
+++ b/spec/support/shared_examples/sign_in.rb
@@ -185,6 +185,74 @@
   end
 end
 
+shared_examples 'signing in as proofed account with broken personal key' do |protocol, sp_ial:|
+  let(:window_start) { 3.days.ago }
+  let(:window_end) { 1.day.ago }
+
+  before do
+    allow(IdentityConfig.store).to receive(:broken_personal_key_window_start).
+      and_return(window_start)
+    allow(IdentityConfig.store).to receive(:broken_personal_key_window_finish).
+      and_return(window_end)
+  end
+
+  def user_with_broken_personal_key(protocol)
+    user = create_ial2_account_go_back_to_sp_and_sign_out(protocol)
+
+    user.active_profile.update(verified_at: window_start + 1.hour)
+    user.update(encrypted_recovery_code_digest_generated_at: nil)
+
+    user
+  end
+
+  context "protocol: #{protocol}, ial: #{sp_ial}" do
+    it 'prompts the user to get a new personal key when signing in with email/password' do
+      user = user_with_broken_personal_key(protocol)
+
+      case sp_ial
+      when 1
+        visit_idp_from_sp_with_ial2(protocol)
+      when 2
+        visit_idp_from_sp_with_ial1(protocol)
+      else
+        raise "unknown sp_ial=#{sp_ial}"
+      end
+
+      fill_in_credentials_and_submit(user.email, user.password)
+
+      expect(page).to have_content(t('account.personal_key.needs_new'))
+      code = page.all('[data-personal-key]').map(&:text).join(' ')
+      click_acknowledge_personal_key
+
+      expect(user.reload.valid_personal_key?(code)).to eq(true)
+      expect(user.active_profile.reload.recover_pii(code)).to be_present
+    end
+
+    it 'prompts for password when signing in via PIV/CAC' do
+      user = user_with_broken_personal_key(protocol)
+
+      create(:piv_cac_configuration, user: user)
+
+      visit_idp_from_sp_with_ial1(protocol)
+      click_on t('account.login.piv_cac')
+      fill_in_piv_cac_credentials_and_submit(user)
+
+      expect(page).to have_content(t('account.personal_key.needs_new'))
+      expect(page).to have_content(t('headings.passwords.confirm_for_personal_key'))
+
+      fill_in t('forms.password'), with: user.password
+      click_button t('forms.buttons.submit.default')
+
+      expect(page).to have_content(t('account.personal_key.needs_new'))
+      code = page.all('[data-personal-key]').map(&:text).join(' ')
+      click_acknowledge_personal_key
+
+      expect(user.reload.valid_personal_key?(code)).to eq(true)
+      expect(user.active_profile.reload.recover_pii(code)).to be_present
+    end
+  end
+end
+
 def personal_key_for_ial2_user(user, pii)
   pii_attrs = Pii::Attributes.new_from_hash(pii)
   profile = user.profiles.last