diff --git a/activerecord/lib/active_record/connection_adapters/abstract/transaction.rb b/activerecord/lib/active_record/connection_adapters/abstract/transaction.rb
index e1f6410cfc..757ea75759 100644
--- a/activerecord/lib/active_record/connection_adapters/abstract/transaction.rb
+++ b/activerecord/lib/active_record/connection_adapters/abstract/transaction.rb
@@ -317,25 +317,31 @@ module ActiveRecord
           end
           raise
         ensure
-          if !error && transaction
-            if Thread.current.status == "aborting"
-              rollback_transaction
+          if transaction
+            if error
+              # @connection still holds an open transaction, so we must not
+              # put it back in the pool for reuse
+              @connection.throw_away! unless transaction.state.rolledback?
             else
-              if !completed && transaction.written
-                ActiveSupport::Deprecation.warn(<<~EOW)
-                  Using `return`, `break` or `throw` to exit a transaction block is
-                  deprecated without replacement. If the `throw` came from
-                  `Timeout.timeout(duration)`, pass an exception class as a second
-                  argument so it doesn't use `throw` to abort its block. This results
-                  in the transaction being committed, but in the next release of Rails
-                  it will rollback.
-                EOW
-              end
-              begin
-                commit_transaction
-              rescue Exception
-                rollback_transaction(transaction) unless transaction.state.completed?
-                raise
+              if Thread.current.status == "aborting"
+                rollback_transaction
+              else
+                if !completed && transaction.written
+                  ActiveSupport::Deprecation.warn(<<~EOW)
+                    Using `return`, `break` or `throw` to exit a transaction block is
+                    deprecated without replacement. If the `throw` came from
+                    `Timeout.timeout(duration)`, pass an exception class as a second
+                    argument so it doesn't use `throw` to abort its block. This results
+                    in the transaction being committed, but in the next release of Rails
+                    it will rollback.
+                  EOW
+                end
+                begin
+                  commit_transaction
+                rescue Exception
+                  rollback_transaction(transaction) unless transaction.state.completed?
+                  raise
+                end
               end
             end
           end
diff --git a/activerecord/lib/active_record/connection_adapters/abstract_adapter.rb b/activerecord/lib/active_record/connection_adapters/abstract_adapter.rb
index e3ca0f85b3..70b4fbd266 100644
--- a/activerecord/lib/active_record/connection_adapters/abstract_adapter.rb
+++ b/activerecord/lib/active_record/connection_adapters/abstract_adapter.rb
@@ -501,6 +501,12 @@ module ActiveRecord
         # this should be overridden by concrete adapters
       end
 
+      # Removes the connection from the pool and disconnect it.
+      def throw_away!
+        pool.remove self
+        disconnect!
+      end
+
       # Clear any caching the database adapter may be doing.
       def clear_cache!
         @lock.synchronize { @statements.clear } if @statements
diff --git a/activerecord/test/cases/transactions_test.rb b/activerecord/test/cases/transactions_test.rb
index f782126ba2..6c0142627e 100644
--- a/activerecord/test/cases/transactions_test.rb
+++ b/activerecord/test/cases/transactions_test.rb
@@ -30,6 +30,53 @@ class TransactionTest < ActiveRecord::TestCase
     assert_equal title_change, topic.changes["title"]
   end
 
+  if !in_memory_db?
+    def test_rollback_dirty_changes_even_with_raise_during_rollback_removes_from_pool
+      topic = topics(:fifth)
+
+      connection = Topic.connection
+
+      Topic.connection.class_eval do
+        alias :real_exec_rollback_db_transaction :exec_rollback_db_transaction
+        define_method(:exec_rollback_db_transaction) do
+          raise
+        end
+      end
+
+      ActiveRecord::Base.transaction do
+        topic.update(title: "Rails is broken")
+        raise ActiveRecord::Rollback
+      end
+
+      assert_not connection.active?
+      assert_not Topic.connection_pool.connections.include?(connection)
+    end
+
+    def test_rollback_dirty_changes_even_with_raise_during_rollback_doesnt_commit_transaction
+      topic = topics(:fifth)
+
+      Topic.connection.class_eval do
+        alias :real_exec_rollback_db_transaction :exec_rollback_db_transaction
+        define_method(:exec_rollback_db_transaction) do
+          raise
+        end
+      end
+
+      ActiveRecord::Base.transaction do
+        topic.update(title: "Rails is broken")
+        raise ActiveRecord::Rollback
+      end
+
+      topic.reload
+
+      ActiveRecord::Base.transaction do
+        topic.update(content: "Ruby on Rails - modified")
+      end
+
+      assert_equal "The Fifth Topic of the day", topic.reload.title
+    end
+  end
+
   def test_rollback_dirty_changes_multiple_saves
     topic = topics(:fifth)