diff --git a/lib/mongo/session.rb b/lib/mongo/session.rb
index 18b27200de..5df118199f 100644
--- a/lib/mongo/session.rb
+++ b/lib/mongo/session.rb
@@ -456,13 +456,26 @@ def with_transaction(options = nil)
                    Utils.monotonic_time + 120
                  end
       transaction_in_progress = false
+      transaction_attempt = 0
+      last_error = nil
+
       loop do
+        if transaction_attempt > 0
+          backoff = backoff_seconds_for_retry(transaction_attempt)
+          if backoff_would_exceed_deadline?(deadline, backoff)
+            raise(last_error)
+          end
+          sleep(backoff)
+        end
+
         commit_options = {}
         if options
           commit_options[:write_concern] = options[:write_concern]
         end
         start_transaction(options)
         transaction_in_progress = true
+        transaction_attempt += 1
+
         begin
           rv = yield self
         rescue Exception => e
@@ -479,6 +492,7 @@ def with_transaction(options = nil)
           end
 
           if e.is_a?(Mongo::Error) && e.label?('TransientTransactionError')
+            last_error = e
             next
           end
 
@@ -495,7 +509,7 @@ def with_transaction(options = nil)
             return rv
           rescue Mongo::Error => e
             if e.label?('UnknownTransactionCommitResult')
-              if  deadline_expired?(deadline) ||
+              if deadline_expired?(deadline) ||
                 e.is_a?(Error::OperationFailure::Family) && e.max_time_ms_expired?
               then
                 transaction_in_progress = false
@@ -516,6 +530,7 @@ def with_transaction(options = nil)
                 transaction_in_progress = false
                 raise
               end
+              last_error = e
               @state = NO_TRANSACTION_STATE
               next
             else
@@ -1312,5 +1327,21 @@ def deadline_expired?(deadline)
         Utils.monotonic_time >= deadline
       end
     end
+
+    # Exponential backoff settings for with_transaction retries.
+    BACKOFF_INITIAL = 0.005
+    BACKOFF_MAX = 0.5
+    private_constant :BACKOFF_INITIAL, :BACKOFF_MAX
+
+    def backoff_seconds_for_retry(transaction_attempt)
+      exponential = BACKOFF_INITIAL * (1.5 ** (transaction_attempt - 1))
+      Random.rand * [exponential, BACKOFF_MAX].min
+    end
+
+    def backoff_would_exceed_deadline?(deadline, backoff_seconds)
+      return false if deadline.zero?
+
+      Utils.monotonic_time + backoff_seconds >= deadline
+    end
   end
 end
diff --git a/spec/mongo/session_transaction_prose_spec.rb b/spec/mongo/session_transaction_prose_spec.rb
new file mode 100644
index 0000000000..6340504c75
--- /dev/null
+++ b/spec/mongo/session_transaction_prose_spec.rb
@@ -0,0 +1,93 @@
+# frozen_string_literal: true
+# rubocop:todo all
+
+require 'spec_helper'
+
+describe Mongo::Session do
+  require_topology :replica_set
+  min_server_version '4.4'
+
+  describe 'transactions convenient API prose tests' do
+    let(:client) { authorized_client }
+    let(:admin_client) { authorized_client.use('admin') }
+    let(:collection) { client['session-transaction-prose-test'] }
+
+    before do
+      collection.delete_many
+    end
+
+    after do
+      disable_fail_command
+    end
+
+    # Prose test from:
+    # specifications/source/transactions-convenient-api/tests/README.md
+    # ### Retry Backoff is Enforced
+    it 'adds measurable delay when jitter is enabled' do
+      skip 'failCommand fail point is not available' unless fail_command_available?
+
+      no_backoff_time = with_fixed_jitter(0) do
+        with_commit_failures(13) do
+          measure_with_transaction_time do |session|
+            collection.insert_one({}, session: session)
+          end
+        end
+      end
+
+      with_backoff_time = with_fixed_jitter(1) do
+        with_commit_failures(13) do
+          measure_with_transaction_time do |session|
+            collection.insert_one({}, session: session)
+          end
+        end
+      end
+
+      # Sum of 13 backoffs per spec is approximately 1.8 seconds.
+      expect(with_backoff_time).to be_within(0.5).of(no_backoff_time + 1.8)
+    end
+
+    private
+
+    def measure_with_transaction_time
+      start_time = Mongo::Utils.monotonic_time
+      client.start_session do |session|
+        session.with_transaction do
+          yield(session)
+        end
+      end
+      Mongo::Utils.monotonic_time - start_time
+    end
+
+    def with_fixed_jitter(value)
+      allow(Random).to receive(:rand).and_return(value)
+      yield
+    end
+
+    def with_commit_failures(times)
+      admin_client.command(
+        configureFailPoint: 'failCommand',
+        mode: { times: times },
+        data: {
+          failCommands: ['commitTransaction'],
+          errorCode: 251,
+        },
+      )
+      yield
+    ensure
+      disable_fail_command
+    end
+
+    def disable_fail_command
+      admin_client.command(configureFailPoint: 'failCommand', mode: 'off')
+    rescue Mongo::Error
+      # Ignore cleanup failures.
+    end
+
+    def fail_command_available?
+      admin_client.command(configureFailPoint: 'failCommand', mode: 'off')
+      true
+    rescue Mongo::Error
+      false
+    end
+  end
+end