diff --git a/mysql-test/suite/encryption/r/innodb_encrypt_freed.result b/mysql-test/suite/encryption/r/innodb_encrypt_freed.result
new file mode 100644
index 00000000000..cdcdd17720e
--- /dev/null
+++ b/mysql-test/suite/encryption/r/innodb_encrypt_freed.result
@@ -0,0 +1,96 @@
+SHOW VARIABLES LIKE 'innodb_encrypt%';
+Variable_name	Value
+innodb_encrypt_log	ON
+innodb_encrypt_tables	ON
+innodb_encrypt_temporary_tables	OFF
+innodb_encryption_rotate_key_age	1
+innodb_encryption_rotation_iops	100
+innodb_encryption_threads	1
+SET GLOBAL innodb_encrypt_tables = ON;
+CREATE TABLE t1(f1 BIGINT PRIMARY KEY, f2 int not null,
+f3 int not null, index(f1), index idx_1(f2),
+index(f2, f3)) ENGINE=InnoDB;
+# Wait max 10 min for key encryption threads to encrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+CREATE TABLE t2 (f1 int not null)engine=innodb;
+# restart: --debug=d,ib_log_checkpoint_avoid
+connect con1,localhost,root,,,;
+begin;
+insert into t2 values(1);
+connection default;
+set global innodb_encrypt_tables = OFF;
+# Wait max 10 min for key encryption threads to decrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+test/t2
+alter table t1 drop index idx_1;
+set global innodb_encrypt_tables = ON;
+# Wait max 10 min for key encryption threads to encrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+test/t2
+disconnect con1;
+# restart: --debug=d,ib_log_checkpoint_avoid
+drop table t1, t2;
+CREATE TABLE t1(f1 BIGINT PRIMARY KEY, f2 int not null,
+f3 int not null, index(f1), index idx_1(f2),
+index(f2, f3)) ENGINE=InnoDB;
+# Wait max 10 min for key encryption threads to encrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+CREATE TABLE t2 (f1 int not null)engine=innodb;
+# restart: --debug=d,ib_log_checkpoint_avoid
+connect con1,localhost,root,,,;
+begin;
+insert into t2 values(1);
+connection default;
+set global innodb_encrypt_tables = OFF;
+# Wait max 10 min for key encryption threads to decrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+test/t2
+alter table t1 drop index idx_1;
+disconnect con1;
+# restart: --debug=d,ib_log_checkpoint_avoid
+connect con1,localhost,root,,,;
+begin;
+insert into t2 values(1);
+connection default;
+set global innodb_encrypt_tables = ON;
+# Wait max 10 min for key encryption threads to encrypt all spaces
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+NAME
+innodb_system
+mysql/innodb_index_stats
+mysql/innodb_table_stats
+mysql/transaction_registry
+test/t1
+test/t2
+disconnect con1;
+drop table t2, t1;
diff --git a/mysql-test/suite/encryption/t/innodb_encrypt_freed.opt b/mysql-test/suite/encryption/t/innodb_encrypt_freed.opt
new file mode 100644
index 00000000000..221e38367f5
--- /dev/null
+++ b/mysql-test/suite/encryption/t/innodb_encrypt_freed.opt
@@ -0,0 +1,4 @@
+--innodb-encrypt-tables
+--innodb-encrypt-log
+--innodb-encryption-threads=1
+--innodb-tablespaces-encryption
diff --git a/mysql-test/suite/encryption/t/innodb_encrypt_freed.test b/mysql-test/suite/encryption/t/innodb_encrypt_freed.test
new file mode 100644
index 00000000000..785b4e9e498
--- /dev/null
+++ b/mysql-test/suite/encryption/t/innodb_encrypt_freed.test
@@ -0,0 +1,117 @@
+--source include/have_innodb.inc
+--source include/have_example_key_management_plugin.inc
+--source include/have_debug.inc
+--source include/not_embedded.inc
+
+SHOW VARIABLES LIKE 'innodb_encrypt%';
+
+SET GLOBAL innodb_encrypt_tables = ON;
+
+CREATE TABLE t1(f1 BIGINT PRIMARY KEY, f2 int not null,
+		f3 int not null, index(f1), index idx_1(f2),
+		index(f2, f3)) ENGINE=InnoDB;
+--let $tables_count= `select count(*) + 1 from information_schema.tables where engine = 'InnoDB'`
+
+--echo # Wait max 10 min for key encryption threads to encrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+
+CREATE TABLE t2 (f1 int not null)engine=innodb;
+let $restart_parameters="--debug=d,ib_log_checkpoint_avoid";
+--source include/restart_mysqld.inc
+
+# Stop the purge
+connect(con1,localhost,root,,,);
+begin;
+insert into t2 values(1);
+
+connection default;
+
+--let $tables_count= `select count(*) + 1 from information_schema.tables where engine = 'InnoDB'`
+set global innodb_encrypt_tables = OFF;
+
+--echo # Wait max 10 min for key encryption threads to decrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+
+# Free the index `idx_1`
+alter table t1 drop index idx_1;
+
+set global innodb_encrypt_tables = ON;
+
+--echo # Wait max 10 min for key encryption threads to encrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+
+disconnect con1;
+let $shutdown_timeout=0;
+--source include/restart_mysqld.inc
+
+drop table t1, t2;
+
+#
+#
+CREATE TABLE t1(f1 BIGINT PRIMARY KEY, f2 int not null,
+		f3 int not null, index(f1), index idx_1(f2),
+		index(f2, f3)) ENGINE=InnoDB;
+--let $tables_count= `select count(*) + 1 from information_schema.tables where engine = 'InnoDB'`
+
+--echo # Wait max 10 min for key encryption threads to encrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+
+CREATE TABLE t2 (f1 int not null)engine=innodb;
+--source include/restart_mysqld.inc
+
+# Stop the purge
+connect(con1,localhost,root,,,);
+begin;
+insert into t2 values(1);
+
+connection default;
+
+--let $tables_count= `select count(*) + 1 from information_schema.tables where engine = 'InnoDB'`
+set global innodb_encrypt_tables = OFF;
+
+--echo # Wait max 10 min for key encryption threads to decrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION = 0;
+
+# Free the index `idx_1`
+alter table t1 drop index idx_1;
+
+disconnect con1;
+--source include/restart_mysqld.inc
+
+# Stop the purge
+connect(con1,localhost,root,,,);
+begin;
+insert into t2 values(1);
+
+connection default;
+set global innodb_encrypt_tables = ON;
+
+--echo # Wait max 10 min for key encryption threads to encrypt all spaces
+--let $wait_timeout= 600
+--let $wait_condition=SELECT COUNT(*) >= $tables_count FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+--source include/wait_condition.inc
+--sorted_result
+SELECT NAME FROM INFORMATION_SCHEMA.INNODB_TABLESPACES_ENCRYPTION WHERE MIN_KEY_VERSION <> 0;
+
+disconnect con1;
+drop table t2, t1;
diff --git a/mysql-test/suite/encryption/t/innodb_encryption.test b/mysql-test/suite/encryption/t/innodb_encryption.test
index a1abfb51462..1c8d200458a 100644
--- a/mysql-test/suite/encryption/t/innodb_encryption.test
+++ b/mysql-test/suite/encryption/t/innodb_encryption.test
@@ -14,7 +14,7 @@ SHOW VARIABLES LIKE 'innodb_encrypt%';
 
 SET GLOBAL innodb_encrypt_tables = ON;
 
---let $tables_count= `select count(*) + 1 from information_schema.tables where engine = 'InnoDB'`
+--let $tables_count= `select count(*) + @@global.innodb_undo_tablespaces + 1 from information_schema.tables where engine = 'InnoDB'`
 
 --echo # Wait max 10 min for key encryption threads to encrypt all spaces
 --let $wait_timeout= 600
diff --git a/storage/innobase/buf/buf0dump.cc b/storage/innobase/buf/buf0dump.cc
index c62c0112e92..c6ddcb4fa48 100644
--- a/storage/innobase/buf/buf0dump.cc
+++ b/storage/innobase/buf/buf0dump.cc
@@ -332,6 +332,10 @@ buf_dump(
 			continue;
 		}
 
+		if (bpage->status == buf_page_t::FREED) {
+			continue;
+		}
+
 		dump[j++] = id;
 	}
 
diff --git a/storage/innobase/fil/fil0crypt.cc b/storage/innobase/fil/fil0crypt.cc
index 26c73e7d0eb..2a8fa875e90 100644
--- a/storage/innobase/fil/fil0crypt.cc
+++ b/storage/innobase/fil/fil0crypt.cc
@@ -1771,6 +1771,11 @@ fil_crypt_get_page_throttle_func(
 		return NULL;
 	}
 
+	if (fseg_page_is_free(space, state->offset)) {
+		/* page is already freed */
+		return NULL;
+	}
+
 	state->crypt_stat.pages_read_from_disk++;
 
 	const ulonglong start = my_interval_timer();
@@ -1874,6 +1879,9 @@ fil_crypt_rotate_page(
 			some dummy pages will be allocated, with 0 in
 			the FIL_PAGE_TYPE. Those pages should be
 			skipped from key rotation forever. */
+		} else if (block->page.status == buf_page_t::FREED) {
+			/* Do not modify freed pages to avoid an assertion
+			failure on recovery.*/
 		} else if (fil_crypt_needs_rotation(
 				crypt_data,
 				kv,
diff --git a/storage/innobase/fsp/fsp0fsp.cc b/storage/innobase/fsp/fsp0fsp.cc
index 1c88d98c3b8..8b821755227 100644
--- a/storage/innobase/fsp/fsp0fsp.cc
+++ b/storage/innobase/fsp/fsp0fsp.cc
@@ -2705,10 +2705,11 @@ fseg_free_step(
 		DBUG_RETURN(true);
 	}
 
-	fseg_free_page_low(
-		inode, iblock, space,
-		fseg_get_nth_frag_page_no(inode, n),
-		mtr);
+	page_no_t page_no = fseg_get_nth_frag_page_no(inode, n);
+
+	fseg_free_page_low(inode, iblock, space, page_no, mtr);
+
+	buf_page_free(space, page_no, mtr, __FILE__, __LINE__);
 
 	n = fseg_find_last_used_frag_page_slot(inode);
 
@@ -2770,6 +2771,7 @@ fseg_free_step_not_header(
 	}
 
 	fseg_free_page_low(inode, iblock, space, page_no, mtr);
+	buf_page_free(space, page_no, mtr, __FILE__, __LINE__);
 	return false;
 }