diff --git a/app/models/concerns/tokenable.rb b/app/models/concerns/tokenable.rb
index ee795186ab..eb5b26d215 100644
--- a/app/models/concerns/tokenable.rb
+++ b/app/models/concerns/tokenable.rb
@@ -28,7 +28,7 @@ def generate_hashed_token(attribute, length: 64, version: ALGO_VERSION)
         # length, since the first 66 chars of our string consist of the account
         # and the bearer's UUID. This lets us use larger tokens (as seen here)
         # and avoid the nasty truncation.
-        res = BCrypt::Password.create Digest::SHA256.digest(raw)
+        res = BCrypt::Password.create Digest::SHA256.hexdigest(raw)
       when "v2"
         raw = SecureRandom.hex(length).gsub /.{#{version.length}}\z/, version
         raw = yield raw if block_given?
@@ -53,6 +53,7 @@ def compare_hashed_token(attribute, token, version: ALGO_VERSION)
 
     a = self.send attribute
     b = nil
+    c = nil
 
     case version
     when "v1"
@@ -64,6 +65,9 @@ def compare_hashed_token(attribute, token, version: ALGO_VERSION)
       end
 
       b = BCrypt::Engine.hash_secret digest, bcrypt.salt
+
+      # FIXME(ezekg) support rehashing: https://github.com/bcrypt-ruby/bcrypt-ruby/pull/168
+      c = BCrypt::Engine.hash_secret Digest::SHA256.hexdigest(token), bcrypt.salt
     when "v2"
       b = OpenSSL::HMAC.hexdigest "SHA512", account.private_key, token
     when "v3"
@@ -72,7 +76,11 @@ def compare_hashed_token(attribute, token, version: ALGO_VERSION)
       raise NotImplementedError.new "token #{version} not implemented"
     end
 
-    secure_compare a, b
+    unless c.nil?
+      secure_compare(a, b) || secure_compare(a, c)
+    else
+      secure_compare(a, b)
+    end
   rescue
     false
   end
diff --git a/app/services/license_key_lookup_service.rb b/app/services/license_key_lookup_service.rb
index f4e05a53be..c7fffd0791 100644
--- a/app/services/license_key_lookup_service.rb
+++ b/app/services/license_key_lookup_service.rb
@@ -22,6 +22,17 @@ def call
       if license&.compare_hashed_token(:key, key, version: 'v1')
         Keygen.logger.warn { "[license-key-lookup-service] v1 keys are deprecated and must be regenerated: license_id=#{license.id.inspect}" }
 
+        # FIXME(ezekg) jit rehash key: https://github.com/bcrypt-ruby/bcrypt-ruby/pull/168
+        digest = BCrypt::Engine.hash_secret(
+          Digest::SHA256.hexdigest(key),
+          BCrypt::Password.new(license.key).salt, # reuse salt
+        )
+        unless license.send(:secure_compare, digest, license.key)
+          Keygen.logger.warn { "[license-key-lookup-service] rehashing key: license_id=#{license.id.inspect}" }
+
+          license.update!(key: digest)
+        end
+
         license
       else
         nil
diff --git a/app/services/token_lookup_service.rb b/app/services/token_lookup_service.rb
index 0874b71a42..8b60ae91b4 100644
--- a/app/services/token_lookup_service.rb
+++ b/app/services/token_lookup_service.rb
@@ -34,6 +34,17 @@ def call
       if instance&.compare_hashed_token(:digest, token, version: 'v1')
         Keygen.logger.warn { "[token-lookup-service] v1 tokens are deprecated and must be regenerated: bearer_type=#{instance.bearer.class.name.inspect} bearer_id=#{instance.bearer.id.inspect} token_id=#{instance.id.inspect}" }
 
+        # FIXME(ezekg) jit rehash token: https://github.com/bcrypt-ruby/bcrypt-ruby/pull/168
+        digest = BCrypt::Engine.hash_secret(
+          Digest::SHA256.hexdigest(token),
+          BCrypt::Password.new(instance.digest).salt, # reuse salt
+        )
+        unless instance.send(:secure_compare, digest, instance.digest)
+          Keygen.logger.warn { "[license-key-lookup-service] rehashing token: token_id=#{instance.id.inspect}" }
+
+          instance.update!(digest:)
+        end
+
         instance
       else
         nil
diff --git a/spec/services/license_key_lookup_service_spec.rb b/spec/services/license_key_lookup_service_spec.rb
new file mode 100644
index 0000000000..254b3c4995
--- /dev/null
+++ b/spec/services/license_key_lookup_service_spec.rb
@@ -0,0 +1,111 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+require 'spec_helper'
+
+describe LicenseKeyLookupService do
+  let(:account) { create(:account) }
+
+  context 'when key is a legacy encrypted key' do
+    let(:key)        { 'bdcecdc23c0f48229f77357151d1e67f-8e1ae3236636bfe57893b835871553eb-524ffec53ad05c14bbf3339eec741300-295512a0539cd0863abe42ddc29cf9v1' }
+    let(:license_id) { key.split('-').first }
+
+    context 'when key is a good key' do
+      let(:digest) { '$2a$12$kh33FHu.TWYMZlWldcOMKet4YiVNqMHq8/A343/GTfPz.NRCPq2Q.' }
+
+      subject! {
+        create(:license, id: license_id, key: digest, account:)
+      }
+
+      it 'should fail unencrypted lookup' do
+        record = described_class.call(key:, account:)
+
+        expect(record).to be nil
+      end
+
+      it 'should pass encrypted lookup' do
+        record = described_class.call(key:, account:, legacy_encrypted: true)
+
+        expect(record).to eq subject
+      end
+
+      it 'should not rehash' do
+        expect { described_class.call(key:, account:, legacy_encrypted: true) }.to_not(
+          change { subject.reload.key },
+        )
+      end
+    end
+
+    context 'when key is a bad key' do
+      let(:digest) { '$2a$12$kh33FHu.TWYMZlWldcOMKevM0Jj4VrN/8.EbfAj4cBEcS51A7hYUK' }
+
+      subject!{
+        create(:license, id: license_id, key: digest, account:)
+      }
+
+      it 'should fail unencrypted lookup' do
+        record = described_class.call(key:, account:)
+
+        expect(record).to be nil
+      end
+
+      it 'should pass encrypted lookup' do
+        record = described_class.call(key:, account:, legacy_encrypted: true)
+
+        expect(record).to eq subject
+      end
+
+      it 'should rehash' do
+        expect { described_class.call(key:, account:, legacy_encrypted: true) }.to(
+          change { subject.reload.key },
+        )
+
+        # sanity check
+        ok = subject.compare_hashed_token(:key, key, version: 'v1')
+        expect(ok).to be true
+      end
+    end
+  end
+
+  context 'when key is a normal key' do
+    let(:key) { 'FC1ECF-659627-58D58E-42130E-ADD88F-V3' }
+
+    subject! {
+      create(:license, key:, account:)
+    }
+
+    it 'should pass unencrypted lookup' do
+      record = described_class.call(key:, account:)
+
+      expect(record).to eq subject
+    end
+
+    it 'should fail encrypted lookup' do
+      record = described_class.call(key:, account:, legacy_encrypted: true)
+
+      expect(record).to be nil
+    end
+
+    it 'should not rehash' do
+      expect { described_class.call(key:, account:) }.to_not(
+        change { subject.reload.key },
+      )
+    end
+  end
+
+  context 'when key is invalid' do
+    let(:key) { '6798CE-A9478B-42027F-4046E8-3FFD66-V3' }
+
+    it 'should fail unencrypted lookup' do
+      record = described_class.call(key:, account:)
+
+      expect(record).to be nil
+    end
+
+    it 'should fail encrypted lookup' do
+      record = described_class.call(key:, account:, legacy_encrypted: true)
+
+      expect(record).to be nil
+    end
+  end
+end
diff --git a/spec/services/token_lookup_service_spec.rb b/spec/services/token_lookup_service_spec.rb
new file mode 100644
index 0000000000..3e3ecd637d
--- /dev/null
+++ b/spec/services/token_lookup_service_spec.rb
@@ -0,0 +1,128 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+require 'spec_helper'
+
+describe TokenLookupService do
+  context 'when token is a v1 token' do
+    let(:token)     { '1780aeccbbb14b4dad0cf8b8165faba2.52f61713fd0c49a2a6537e3142d043cb.3e2373c60b7df8514ff763dad707faad44956c2421fdb2588fff2a73099b07v1' }
+    let(:account_id) { token.split('.').first }
+    let(:token_id)   { token.split('.').second }
+    let(:account)    { create(:account, id: account_id) }
+    let(:product)    { create(:product, account:) }
+
+    context 'when token is a good token' do
+      let(:digest) { '$2a$12$7sgr9E9ZURyXzttcuIl/muYRww.wHxNgCpgUHsKODV2ZXpPWiqLkq' }
+
+      subject! {
+        record = create(:token, id: token_id, bearer: product, account:)
+        record.update!(digest:)
+        record
+      }
+
+      it 'should pass lookup' do
+        record = described_class.call(token:, account:)
+
+        expect(record).to eq subject
+      end
+
+      it 'should not rehash' do
+        expect { described_class.call(token:, account:) }.to_not(
+          change { subject.reload.digest },
+        )
+      end
+    end
+
+    context 'when token is a bad token' do
+      let(:digest) { '$2a$12$7sgr9E9ZURyXzttcuIl/muSl7JViEcBcytnbouQooX22PP43AzZ4C' }
+
+      subject! {
+        record = create(:token, id: token_id, bearer: product, account:)
+        record.update!(digest:)
+        record
+      }
+
+      it 'should pass lookup' do
+        record = described_class.call(token:, account:)
+
+        expect(record).to eq subject
+      end
+
+      it 'should rehash' do
+        expect { described_class.call(token:, account:) }.to(
+          change { subject.reload.digest },
+        )
+
+        # sanity check
+        ok = subject.compare_hashed_token(:digest, token, version: 'v1')
+        expect(ok).to be true
+      end
+    end
+  end
+
+  context 'when token is a v2 token' do
+    let(:token)   { 'prod-c5cf2bc0986bb90cae46dade120172c1451abfc3429a4f9057a9786738d192v2' }
+    let(:digest)  { '0c8f765a79a45992c1031f8cc69b858a960257ee16bfd67e26487913565e04337c25897b62011d45b75a7bc20a7e16057fef2573d32f91c1f264f595cfdd2a04' }
+    let(:account) { create(:account) }
+    let(:product) { create(:product, account:) }
+
+    subject! {
+      record = create(:token, bearer: product, account:)
+      record.update!(digest:)
+      record
+    }
+
+    it 'should pass lookup' do
+      record = described_class.call(token:, account:)
+
+      expect(record).to eq subject
+    end
+
+    it 'should not rehash' do
+      expect { described_class.call(token:, account:) }.to_not(
+        change { subject.reload.digest },
+      )
+    end
+  end
+
+  context 'when token is a v3 token' do
+    let(:secret_key) { '9ef57edb7f2a91bed90805744cdbf4ece13905ad2670bc1f54212074043cede710ca6a60c95114cf16fbbef7d696b0c61649250a9baf14aab878e5f85f769836' }
+    let(:token)      { 'prod-580839d4388a61216398c83f2c987a80dee472f556db7bc9aa66775574de54f4v3' }
+    let(:digest)     { '0e555b39a256a319674356f834d39de70c06b0d0ef94f4b8f9c7d34bdc287f93' }
+    let(:product)    { create(:product, account:) }
+    let(:account)    {
+      record = create(:account)
+      record.update(secret_key:)
+      record
+    }
+
+    subject! {
+      record = create(:token, bearer: product, account:)
+      record.update!(digest:)
+      record
+    }
+
+    it 'should pass lookup' do
+      record = described_class.call(token:, account:)
+
+      expect(record).to eq subject
+    end
+
+    it 'should not rehash' do
+      expect { described_class.call(token:, account:) }.to_not(
+        change { subject.reload.digest },
+      )
+    end
+  end
+
+  context 'when token is invalid' do
+    let(:token)   { 'user-f25149752c704e0c8281150c6751ba77052111ad14214d5adacd0a80d45cc957v3' }
+    let(:account) { create(:account) }
+
+    it 'should fail lookup' do
+      record = described_class.call(token:, account:)
+
+      expect(record).to be nil
+    end
+  end
+end