[Openvpn-devel,v4,1/2] crypto: always reload tls-auth/crypt key contexts

Message ID 20180707090421.25953-1-a@unstable.cc
State Superseded
Headers show
Series
  • [Openvpn-devel,v4,1/2] crypto: always reload tls-auth/crypt key contexts
Related show

Commit Message

Antonio Quartulli July 7, 2018, 9:04 a.m.
In preparation to having tls-auth/crypt keys per connection
block, it is important to ensure that such material is always
reloaded upon SIGUSR1, no matter if `persist-key` was specified
or not.

This is required because when moving from one remote to the
other the key may change and thus the key context needs to
be refreshed.

To ensure that the `persist-key` logic will still work
as expected, the tls-auth/crypt key is pre-loaded so that
the keyfile is not required at runtime.

Trac: #720
Cc: Steffan Karger <steffan@karger.me>
Signed-off-by: Antonio Quartulli <a@unstable.cc>
---
v2:
- introduce this patch
v3:
- add key per-loading logic to this patch to avoid temporary features
  breakages
v4:
- rebase on top of master
- use buffer_read_from_file() implementation from "tls-crypt-v2: generate
  client keys". Minor change: in case of error, free buffer and remove
  it from gc (with new free_buf_gc()), if provided.
- don't go FATAL inside buffer_read_from_file() in case of error, but
  let external logic decide

 src/openvpn/buffer.c  | 61 ++++++++++++++++++++++++++++++
 src/openvpn/buffer.h  | 12 ++++++
 src/openvpn/crypto.c  | 21 +++--------
 src/openvpn/init.c    | 87 ++++++++++++++++++++++++++++---------------
 src/openvpn/options.c | 26 +++++++++++++
 5 files changed, 161 insertions(+), 46 deletions(-)

Comments

Steffan Karger July 7, 2018, 12:45 p.m. | #1
Hi,

On 07-07-18 11:04, Antonio Quartulli wrote:
> In preparation to having tls-auth/crypt keys per connection
> block, it is important to ensure that such material is always
> reloaded upon SIGUSR1, no matter if `persist-key` was specified
> or not.
> 
> This is required because when moving from one remote to the
> other the key may change and thus the key context needs to
> be refreshed.
> 
> To ensure that the `persist-key` logic will still work
> as expected, the tls-auth/crypt key is pre-loaded so that
> the keyfile is not required at runtime.
> 
> Trac: #720
> Cc: Steffan Karger <steffan@karger.me>
> Signed-off-by: Antonio Quartulli <a@unstable.cc>
> ---
> v2:
> - introduce this patch
> v3:
> - add key per-loading logic to this patch to avoid temporary features
>   breakages
> v4:
> - rebase on top of master
> - use buffer_read_from_file() implementation from "tls-crypt-v2: generate
>   client keys". Minor change: in case of error, free buffer and remove
>   it from gc (with new free_buf_gc()), if provided.
> - don't go FATAL inside buffer_read_from_file() in case of error, but
>   let external logic decide
> 
>  src/openvpn/buffer.c  | 61 ++++++++++++++++++++++++++++++
>  src/openvpn/buffer.h  | 12 ++++++
>  src/openvpn/crypto.c  | 21 +++--------
>  src/openvpn/init.c    | 87 ++++++++++++++++++++++++++++---------------
>  src/openvpn/options.c | 26 +++++++++++++
>  5 files changed, 161 insertions(+), 46 deletions(-)
> 
> diff --git a/src/openvpn/buffer.c b/src/openvpn/buffer.c
> index becfeb93..7d4860db 100644
> --- a/src/openvpn/buffer.c
> +++ b/src/openvpn/buffer.c
> @@ -189,6 +189,34 @@ free_buf(struct buffer *buf)
>      CLEAR(*buf);
>  }
>  
> +static void
> +free_buf_gc(struct buffer *buf, struct gc_arena *gc)
> +{
> +    if (gc)
> +    {
> +        struct gc_entry **e = &gc->list;
> +
> +        while (*e)
> +        {
> +            /* check if this object is the one we want to delete */
> +            if ((uint8_t *)((*e) + sizeof(*e)) == buf->data)

I think this should be sizeof(**e).

> +            {
> +                struct gc_entry *to_delete = *e;
> +
> +                /* remove element from linked list and free it */
> +                *e = (*e)->next;
> +                free(to_delete);
> +
> +                break;
> +            }
> +
> +            e = &(*e)->next;
> +        }
> +    }
> +
> +    free_buf(buf);
> +}
> +
>  /*
>   * Return a buffer for write that is a subset of another buffer
>   */
> @@ -1332,3 +1360,36 @@ buffer_list_file(const char *fn, int max_line_len)
>      }
>      return bl;
>  }
> +
> +struct buffer
> +buffer_read_from_file(const char *filename, struct gc_arena *gc)
> +{
> +    struct buffer ret = { 0 };
> +
> +    platform_stat_t file_stat = {0};
> +    if (platform_stat(filename, &file_stat) < 0)
> +    {
> +        return ret;
> +    }
> +
> +    FILE *fp = platform_fopen(filename, "r");
> +    if (!fp)
> +    {
> +        return ret;
> +    }
> +
> +    const size_t size = file_stat.st_size;
> +    ret = alloc_buf_gc(size + 1, gc); /* space for trailing \0 */
> +    ssize_t read_size = fread(BPTR(&ret), 1, size, fp);
> +    if (read_size < 0)
> +    {
> +        free_buf_gc(&ret, gc);
> +        goto cleanup;
> +    }
> +    ASSERT(buf_inc_len(&ret, read_size));
> +    buf_null_terminate(&ret);
> +
> +cleanup:
> +    fclose(fp);
> +    return ret;
> +}
> diff --git a/src/openvpn/buffer.h b/src/openvpn/buffer.h
> index d848490a..a11c8bd9 100644
> --- a/src/openvpn/buffer.h
> +++ b/src/openvpn/buffer.h
> @@ -1112,4 +1112,16 @@ void buffer_list_aggregate_separator(struct buffer_list *bl,
>  
>  struct buffer_list *buffer_list_file(const char *fn, int max_line_len);
>  
> +/**
> + * buffer_read_from_file - copy the content of a file into a buffer
> + *
> + * @param file      path to the file to read
> + * @param gc        the garbage collector to use when allocating the buffer. It
> + *                  passed to alloc_buf_gc() and therefore can be NULL.

It *is* passed ?

> + *
> + * @return the buffer storing the file content or an invalid buffer in case of
> + * error
> + */
> +struct buffer buffer_read_from_file(const char *filename, struct gc_arena *gc);
> +
>  #endif /* BUFFER_H */
> diff --git a/src/openvpn/crypto.c b/src/openvpn/crypto.c
> index b59c1f73..5381ef2a 100644
> --- a/src/openvpn/crypto.c
> +++ b/src/openvpn/crypto.c
> @@ -1224,7 +1224,7 @@ read_key_file(struct key2 *key2, const char *file, const unsigned int flags)
>  {
>      struct gc_arena gc = gc_new();
>      struct buffer in;
> -    int fd, size;
> +    int size;
>      uint8_t hex_byte[3] = {0, 0, 0};
>      const char *error_filename = file;
>  
> @@ -1268,22 +1268,11 @@ read_key_file(struct key2 *key2, const char *file, const unsigned int flags)
>      }
>      else /* 'file' is a filename which refers to a file containing the ascii key */
>      {
> -        in = alloc_buf_gc(2048, &gc);
> -        fd = platform_open(file, O_RDONLY, 0);
> -        if (fd == -1)
> -        {
> -            msg(M_ERR, "Cannot open key file '%s'", file);
> -        }
> -        size = read(fd, in.data, in.capacity);
> -        if (size < 0)
> -        {
> +        in = buffer_read_from_file(file, &gc);
> +        if (!buf_valid(&in))
>              msg(M_FATAL, "Read error on key file ('%s')", file);
> -        }
> -        if (size == in.capacity)
> -        {
> -            msg(M_FATAL, "Key file ('%s') can be a maximum of %d bytes", file, (int)in.capacity);
> -        }
> -        close(fd);
> +
> +        size = in.len;
>      }
>  
>      cp = (unsigned char *)in.data;
> diff --git a/src/openvpn/init.c b/src/openvpn/init.c
> index b748357d..1b46b364 100644
> --- a/src/openvpn/init.c
> +++ b/src/openvpn/init.c
> @@ -2409,7 +2409,6 @@ key_schedule_free(struct key_schedule *ks, bool free_ssl_ctx)
>      if (tls_ctx_initialised(&ks->ssl_ctx) && free_ssl_ctx)
>      {
>          tls_ctx_free(&ks->ssl_ctx);
> -        free_key_ctx_bi(&ks->tls_wrap_key);
>      }
>      CLEAR(*ks);
>  }
> @@ -2499,6 +2498,48 @@ do_init_crypto_static(struct context *c, const unsigned int flags)
>      check_replay_consistency(&c->c1.ks.key_type, options->replay);
>  }
>  
> +/*
> + * Initialize the tls-auth/crypt key context
> + */
> +static void
> +do_init_tls_wrap_key(struct context *c)
> +{
> +    const struct options *options = &c->options;
> +
> +    /* TLS handshake authentication (--tls-auth) */
> +    if (options->tls_auth_file)
> +    {
> +        /* Initialize key_type for tls-auth with auth only */
> +        CLEAR(c->c1.ks.tls_auth_key_type);
> +        if (!streq(options->authname, "none"))
> +        {
> +            c->c1.ks.tls_auth_key_type.digest = md_kt_get(options->authname);
> +                c->c1.ks.tls_auth_key_type.hmac_length =
> +                    md_kt_size(c->c1.ks.tls_auth_key_type.digest);
> +        }
> +        else
> +        {
> +            msg(M_FATAL, "ERROR: tls-auth enabled, but no valid --auth "
> +                "algorithm specified ('%s')", options->authname);
> +        }
> +
> +        crypto_read_openvpn_key(&c->c1.ks.tls_auth_key_type,
> +                                &c->c1.ks.tls_wrap_key,
> +                                options->tls_auth_file,
> +                                options->tls_auth_file_inline,
> +                                options->key_direction,
> +                                "Control Channel Authentication", "tls-auth");
> +    }
> +
> +    /* TLS handshake encryption+authentication (--tls-crypt) */
> +    if (options->tls_crypt_file)
> +    {
> +        tls_crypt_init_key(&c->c1.ks.tls_wrap_key,
> +                           options->tls_crypt_file,
> +                           options->tls_crypt_inline, options->tls_server);
> +    }
> +}
> +
>  /*
>   * Initialize the persistent component of OpenVPN's TLS mode,
>   * which is preserved across SIGUSR1 resets.
> @@ -2548,35 +2589,8 @@ do_init_crypto_tls_c1(struct context *c)
>          /* Initialize PRNG with config-specified digest */
>          prng_init(options->prng_hash, options->prng_nonce_secret_len);
>  
> -        /* TLS handshake authentication (--tls-auth) */
> -        if (options->tls_auth_file)
> -        {
> -            /* Initialize key_type for tls-auth with auth only */
> -            CLEAR(c->c1.ks.tls_auth_key_type);
> -            if (!streq(options->authname, "none"))
> -            {
> -                c->c1.ks.tls_auth_key_type.digest = md_kt_get(options->authname);
> -                c->c1.ks.tls_auth_key_type.hmac_length =
> -                    md_kt_size(c->c1.ks.tls_auth_key_type.digest);
> -            }
> -            else
> -            {
> -                msg(M_FATAL, "ERROR: tls-auth enabled, but no valid --auth "
> -                    "algorithm specified ('%s')", options->authname);
> -            }
> -
> -            crypto_read_openvpn_key(&c->c1.ks.tls_auth_key_type,
> -                                    &c->c1.ks.tls_wrap_key, options->tls_auth_file,
> -                                    options->tls_auth_file_inline, options->key_direction,
> -                                    "Control Channel Authentication", "tls-auth");
> -        }
> -
> -        /* TLS handshake encryption+authentication (--tls-crypt) */
> -        if (options->tls_crypt_file)
> -        {
> -            tls_crypt_init_key(&c->c1.ks.tls_wrap_key, options->tls_crypt_file,
> -                               options->tls_crypt_inline, options->tls_server);
> -        }
> +        /* initialize tls-auth/crypt key */
> +        do_init_tls_wrap_key(c);
>  
>          c->c1.ciphername = options->ciphername;
>          c->c1.authname = options->authname;
> @@ -2598,6 +2612,12 @@ do_init_crypto_tls_c1(struct context *c)
>          c->options.ciphername = c->c1.ciphername;
>          c->options.authname = c->c1.authname;
>          c->options.keysize = c->c1.keysize;
> +
> +        /*
> +         * tls-auth/crypt key can be configured per connection block, therefore
> +         * we must reload it as it may have changed
> +         */
> +        do_init_tls_wrap_key(c);
>      }
>  }
>  
> @@ -3401,6 +3421,13 @@ do_close_tls(struct context *c)
>  static void
>  do_close_free_key_schedule(struct context *c, bool free_ssl_ctx)
>  {
> +    /*
> +     * always free the tls_auth/crypt key. If persist_key is true, the key will
> +     * be reloaded from memory (pre-cached)
> +     */
> +    free_key_ctx_bi(&c->c1.ks.tls_wrap_key);
> +    CLEAR(c->c1.ks.tls_wrap_key);
> +
>      if (!(c->sig->signal_received == SIGUSR1 && c->options.persist_key))
>      {
>          key_schedule_free(&c->c1.ks, free_ssl_ctx);
> diff --git a/src/openvpn/options.c b/src/openvpn/options.c
> index 426057ab..b2ca2738 100644
> --- a/src/openvpn/options.c
> +++ b/src/openvpn/options.c
> @@ -3019,6 +3019,32 @@ options_postprocess_mutate(struct options *o)
>          options_postprocess_mutate_ce(o, o->connection_list->array[i]);
>      }
>  
> +    /* pre-cache tls-auth/crypt key file if persist-key was specified */
> +    if (o->persist_key)
> +    {
> +        if (o->tls_auth_file && !o->tls_auth_file_inline)
> +        {
> +            struct buffer in = buffer_read_from_file(o->tls_auth_file, &o->gc);
> +            if (!buf_valid(&in))
> +                msg(M_FATAL, "Cannot pre-load tls-auth keyfile (%s)",
> +                    o->tls_auth_file);
> +
> +            o->tls_auth_file = INLINE_FILE_TAG;
> +            o->tls_auth_file_inline = (char *)in.data;
> +        }
> +
> +        if (o->tls_crypt_file && !o->tls_crypt_inline)
> +        {
> +            struct buffer in = buffer_read_from_file(o->tls_crypt_file, &o->gc);
> +            if (!buf_valid(&in))
> +                msg(M_FATAL, "Cannot pre-load tls-crypt keyfile (%s)",
> +                    o->tls_auth_file);
> +
> +            o->tls_crypt_file = INLINE_FILE_TAG;
> +            o->tls_crypt_inline = (char *)in.data;
> +        }
> +    }
> +
>      if (o->tls_server)
>      {
>          /* Check that DH file is specified, or explicitly disabled */
> 

Otherwise, this looks good.

-Steffan

------------------------------------------------------------------------------
Check out the vibrant tech community on one of the world's most
engaging tech sites, Slashdot.org! http://sdm.link/slashdot
Antonio Quartulli July 7, 2018, 4:25 p.m. | #2
Hi,

On 07/07/18 20:45, Steffan Karger wrote:
> Hi,

[cut]

>> +static void
>> +free_buf_gc(struct buffer *buf, struct gc_arena *gc)
>> +{
>> +    if (gc)
>> +    {
>> +        struct gc_entry **e = &gc->list;
>> +
>> +        while (*e)
>> +        {
>> +            /* check if this object is the one we want to delete */
>> +            if ((uint8_t *)((*e) + sizeof(*e)) == buf->data)
> 
> I think this should be sizeof(**e).
> 

Right! Thanks for catching this!

[cut]

>> +/**
>> + * buffer_read_from_file - copy the content of a file into a buffer
>> + *
>> + * @param file      path to the file to read
>> + * @param gc        the garbage collector to use when allocating the buffer. It
>> + *                  passed to alloc_buf_gc() and therefore can be NULL.
> 
> It *is* passed ?
> 

of course :-) thanks!

[cut]

> 
> Otherwise, this looks good.
> 

Cool, thanks!

I will send v4 with these small fixes and a unit test for the
buf_free_gc() function.


Cheers,

Patch

diff --git a/src/openvpn/buffer.c b/src/openvpn/buffer.c
index becfeb93..7d4860db 100644
--- a/src/openvpn/buffer.c
+++ b/src/openvpn/buffer.c
@@ -189,6 +189,34 @@  free_buf(struct buffer *buf)
     CLEAR(*buf);
 }
 
+static void
+free_buf_gc(struct buffer *buf, struct gc_arena *gc)
+{
+    if (gc)
+    {
+        struct gc_entry **e = &gc->list;
+
+        while (*e)
+        {
+            /* check if this object is the one we want to delete */
+            if ((uint8_t *)((*e) + sizeof(*e)) == buf->data)
+            {
+                struct gc_entry *to_delete = *e;
+
+                /* remove element from linked list and free it */
+                *e = (*e)->next;
+                free(to_delete);
+
+                break;
+            }
+
+            e = &(*e)->next;
+        }
+    }
+
+    free_buf(buf);
+}
+
 /*
  * Return a buffer for write that is a subset of another buffer
  */
@@ -1332,3 +1360,36 @@  buffer_list_file(const char *fn, int max_line_len)
     }
     return bl;
 }
+
+struct buffer
+buffer_read_from_file(const char *filename, struct gc_arena *gc)
+{
+    struct buffer ret = { 0 };
+
+    platform_stat_t file_stat = {0};
+    if (platform_stat(filename, &file_stat) < 0)
+    {
+        return ret;
+    }
+
+    FILE *fp = platform_fopen(filename, "r");
+    if (!fp)
+    {
+        return ret;
+    }
+
+    const size_t size = file_stat.st_size;
+    ret = alloc_buf_gc(size + 1, gc); /* space for trailing \0 */
+    ssize_t read_size = fread(BPTR(&ret), 1, size, fp);
+    if (read_size < 0)
+    {
+        free_buf_gc(&ret, gc);
+        goto cleanup;
+    }
+    ASSERT(buf_inc_len(&ret, read_size));
+    buf_null_terminate(&ret);
+
+cleanup:
+    fclose(fp);
+    return ret;
+}
diff --git a/src/openvpn/buffer.h b/src/openvpn/buffer.h
index d848490a..a11c8bd9 100644
--- a/src/openvpn/buffer.h
+++ b/src/openvpn/buffer.h
@@ -1112,4 +1112,16 @@  void buffer_list_aggregate_separator(struct buffer_list *bl,
 
 struct buffer_list *buffer_list_file(const char *fn, int max_line_len);
 
+/**
+ * buffer_read_from_file - copy the content of a file into a buffer
+ *
+ * @param file      path to the file to read
+ * @param gc        the garbage collector to use when allocating the buffer. It
+ *                  passed to alloc_buf_gc() and therefore can be NULL.
+ *
+ * @return the buffer storing the file content or an invalid buffer in case of
+ * error
+ */
+struct buffer buffer_read_from_file(const char *filename, struct gc_arena *gc);
+
 #endif /* BUFFER_H */
diff --git a/src/openvpn/crypto.c b/src/openvpn/crypto.c
index b59c1f73..5381ef2a 100644
--- a/src/openvpn/crypto.c
+++ b/src/openvpn/crypto.c
@@ -1224,7 +1224,7 @@  read_key_file(struct key2 *key2, const char *file, const unsigned int flags)
 {
     struct gc_arena gc = gc_new();
     struct buffer in;
-    int fd, size;
+    int size;
     uint8_t hex_byte[3] = {0, 0, 0};
     const char *error_filename = file;
 
@@ -1268,22 +1268,11 @@  read_key_file(struct key2 *key2, const char *file, const unsigned int flags)
     }
     else /* 'file' is a filename which refers to a file containing the ascii key */
     {
-        in = alloc_buf_gc(2048, &gc);
-        fd = platform_open(file, O_RDONLY, 0);
-        if (fd == -1)
-        {
-            msg(M_ERR, "Cannot open key file '%s'", file);
-        }
-        size = read(fd, in.data, in.capacity);
-        if (size < 0)
-        {
+        in = buffer_read_from_file(file, &gc);
+        if (!buf_valid(&in))
             msg(M_FATAL, "Read error on key file ('%s')", file);
-        }
-        if (size == in.capacity)
-        {
-            msg(M_FATAL, "Key file ('%s') can be a maximum of %d bytes", file, (int)in.capacity);
-        }
-        close(fd);
+
+        size = in.len;
     }
 
     cp = (unsigned char *)in.data;
diff --git a/src/openvpn/init.c b/src/openvpn/init.c
index b748357d..1b46b364 100644
--- a/src/openvpn/init.c
+++ b/src/openvpn/init.c
@@ -2409,7 +2409,6 @@  key_schedule_free(struct key_schedule *ks, bool free_ssl_ctx)
     if (tls_ctx_initialised(&ks->ssl_ctx) && free_ssl_ctx)
     {
         tls_ctx_free(&ks->ssl_ctx);
-        free_key_ctx_bi(&ks->tls_wrap_key);
     }
     CLEAR(*ks);
 }
@@ -2499,6 +2498,48 @@  do_init_crypto_static(struct context *c, const unsigned int flags)
     check_replay_consistency(&c->c1.ks.key_type, options->replay);
 }
 
+/*
+ * Initialize the tls-auth/crypt key context
+ */
+static void
+do_init_tls_wrap_key(struct context *c)
+{
+    const struct options *options = &c->options;
+
+    /* TLS handshake authentication (--tls-auth) */
+    if (options->tls_auth_file)
+    {
+        /* Initialize key_type for tls-auth with auth only */
+        CLEAR(c->c1.ks.tls_auth_key_type);
+        if (!streq(options->authname, "none"))
+        {
+            c->c1.ks.tls_auth_key_type.digest = md_kt_get(options->authname);
+                c->c1.ks.tls_auth_key_type.hmac_length =
+                    md_kt_size(c->c1.ks.tls_auth_key_type.digest);
+        }
+        else
+        {
+            msg(M_FATAL, "ERROR: tls-auth enabled, but no valid --auth "
+                "algorithm specified ('%s')", options->authname);
+        }
+
+        crypto_read_openvpn_key(&c->c1.ks.tls_auth_key_type,
+                                &c->c1.ks.tls_wrap_key,
+                                options->tls_auth_file,
+                                options->tls_auth_file_inline,
+                                options->key_direction,
+                                "Control Channel Authentication", "tls-auth");
+    }
+
+    /* TLS handshake encryption+authentication (--tls-crypt) */
+    if (options->tls_crypt_file)
+    {
+        tls_crypt_init_key(&c->c1.ks.tls_wrap_key,
+                           options->tls_crypt_file,
+                           options->tls_crypt_inline, options->tls_server);
+    }
+}
+
 /*
  * Initialize the persistent component of OpenVPN's TLS mode,
  * which is preserved across SIGUSR1 resets.
@@ -2548,35 +2589,8 @@  do_init_crypto_tls_c1(struct context *c)
         /* Initialize PRNG with config-specified digest */
         prng_init(options->prng_hash, options->prng_nonce_secret_len);
 
-        /* TLS handshake authentication (--tls-auth) */
-        if (options->tls_auth_file)
-        {
-            /* Initialize key_type for tls-auth with auth only */
-            CLEAR(c->c1.ks.tls_auth_key_type);
-            if (!streq(options->authname, "none"))
-            {
-                c->c1.ks.tls_auth_key_type.digest = md_kt_get(options->authname);
-                c->c1.ks.tls_auth_key_type.hmac_length =
-                    md_kt_size(c->c1.ks.tls_auth_key_type.digest);
-            }
-            else
-            {
-                msg(M_FATAL, "ERROR: tls-auth enabled, but no valid --auth "
-                    "algorithm specified ('%s')", options->authname);
-            }
-
-            crypto_read_openvpn_key(&c->c1.ks.tls_auth_key_type,
-                                    &c->c1.ks.tls_wrap_key, options->tls_auth_file,
-                                    options->tls_auth_file_inline, options->key_direction,
-                                    "Control Channel Authentication", "tls-auth");
-        }
-
-        /* TLS handshake encryption+authentication (--tls-crypt) */
-        if (options->tls_crypt_file)
-        {
-            tls_crypt_init_key(&c->c1.ks.tls_wrap_key, options->tls_crypt_file,
-                               options->tls_crypt_inline, options->tls_server);
-        }
+        /* initialize tls-auth/crypt key */
+        do_init_tls_wrap_key(c);
 
         c->c1.ciphername = options->ciphername;
         c->c1.authname = options->authname;
@@ -2598,6 +2612,12 @@  do_init_crypto_tls_c1(struct context *c)
         c->options.ciphername = c->c1.ciphername;
         c->options.authname = c->c1.authname;
         c->options.keysize = c->c1.keysize;
+
+        /*
+         * tls-auth/crypt key can be configured per connection block, therefore
+         * we must reload it as it may have changed
+         */
+        do_init_tls_wrap_key(c);
     }
 }
 
@@ -3401,6 +3421,13 @@  do_close_tls(struct context *c)
 static void
 do_close_free_key_schedule(struct context *c, bool free_ssl_ctx)
 {
+    /*
+     * always free the tls_auth/crypt key. If persist_key is true, the key will
+     * be reloaded from memory (pre-cached)
+     */
+    free_key_ctx_bi(&c->c1.ks.tls_wrap_key);
+    CLEAR(c->c1.ks.tls_wrap_key);
+
     if (!(c->sig->signal_received == SIGUSR1 && c->options.persist_key))
     {
         key_schedule_free(&c->c1.ks, free_ssl_ctx);
diff --git a/src/openvpn/options.c b/src/openvpn/options.c
index 426057ab..b2ca2738 100644
--- a/src/openvpn/options.c
+++ b/src/openvpn/options.c
@@ -3019,6 +3019,32 @@  options_postprocess_mutate(struct options *o)
         options_postprocess_mutate_ce(o, o->connection_list->array[i]);
     }
 
+    /* pre-cache tls-auth/crypt key file if persist-key was specified */
+    if (o->persist_key)
+    {
+        if (o->tls_auth_file && !o->tls_auth_file_inline)
+        {
+            struct buffer in = buffer_read_from_file(o->tls_auth_file, &o->gc);
+            if (!buf_valid(&in))
+                msg(M_FATAL, "Cannot pre-load tls-auth keyfile (%s)",
+                    o->tls_auth_file);
+
+            o->tls_auth_file = INLINE_FILE_TAG;
+            o->tls_auth_file_inline = (char *)in.data;
+        }
+
+        if (o->tls_crypt_file && !o->tls_crypt_inline)
+        {
+            struct buffer in = buffer_read_from_file(o->tls_crypt_file, &o->gc);
+            if (!buf_valid(&in))
+                msg(M_FATAL, "Cannot pre-load tls-crypt keyfile (%s)",
+                    o->tls_auth_file);
+
+            o->tls_crypt_file = INLINE_FILE_TAG;
+            o->tls_crypt_inline = (char *)in.data;
+        }
+    }
+
     if (o->tls_server)
     {
         /* Check that DH file is specified, or explicitly disabled */