diff --git a/include/asterisk/sorcery.h b/include/asterisk/sorcery.h
index a0ec653584..c3e2864ace 100644
--- a/include/asterisk/sorcery.h
+++ b/include/asterisk/sorcery.h
@@ -1558,6 +1558,28 @@ const char *ast_sorcery_object_get_extended(const void *object, const char *name
  */
 int ast_sorcery_object_set_extended(const void *object, const char *name, const char *value);
 
+/*!
+ * \brief Get whether an object contains dynamic contents or not
+ *
+ * \param object Pointer to a sorcery object
+ *
+ * \since 19
+ * \since 18.3.0
+ * \since 16.17.0
+ */
+unsigned int ast_sorcery_object_has_dynamic_contents(const void *object);
+
+/*!
+ * \brief Set the dynamic contents flag on a sorcery object
+ *
+ * \param object Pointer to a sorcery object
+ *
+ * \since 19
+ * \since 18.3.0
+ * \since 16.17.0
+ */
+void ast_sorcery_object_set_has_dynamic_contents(const void *object);
+
 /*!
  * \brief ao2 object comparator based on sorcery id.
  */
diff --git a/main/sorcery.c b/main/sorcery.c
index 0ada81e3f7..ad10aeeeff 100644
--- a/main/sorcery.c
+++ b/main/sorcery.c
@@ -139,6 +139,9 @@ struct ast_sorcery_object {
 
 	/*! \brief Time that the object was created */
 	struct timeval created;
+
+	/*! \brief Whether this object has dynamic contents or not */
+	unsigned int has_dynamic_contents:1;
 };
 
 /*! \brief Structure for registered object type */
@@ -2366,6 +2369,20 @@ int ast_sorcery_object_set_extended(const void *object, const char *name, const
 	return 0;
 }
 
+unsigned int ast_sorcery_object_has_dynamic_contents(const void *object)
+{
+	const struct ast_sorcery_object_details *details = object;
+
+	return details->object->has_dynamic_contents;
+}
+
+void ast_sorcery_object_set_has_dynamic_contents(const void *object)
+{
+	const struct ast_sorcery_object_details *details = object;
+
+	details->object->has_dynamic_contents = 1;
+}
+
 int ast_sorcery_observer_add(const struct ast_sorcery *sorcery, const char *type, const struct ast_sorcery_observer *callbacks)
 {
 	RAII_VAR(struct ast_sorcery_object_type *, object_type, ao2_find(sorcery->types, type, OBJ_KEY), ao2_cleanup);
diff --git a/res/res_pjsip_endpoint_identifier_ip.c b/res/res_pjsip_endpoint_identifier_ip.c
index a2aa934446..d8de26112c 100644
--- a/res/res_pjsip_endpoint_identifier_ip.c
+++ b/res/res_pjsip_endpoint_identifier_ip.c
@@ -515,6 +515,9 @@ static int ip_identify_apply(const struct ast_sorcery *sorcery, void *obj)
 		return 0;
 	}
 
+	/* Hosts can produce dynamic content, so mark the identify as such */
+	ast_sorcery_object_set_has_dynamic_contents(obj);
+
 	/* Resolve the match addresses now */
 	i = ao2_iterator_init(identify->hosts, 0);
 	while ((current_string = ao2_iterator_next(&i))) {
diff --git a/res/res_sorcery_config.c b/res/res_sorcery_config.c
index 67679a2280..dfe7a351ed 100644
--- a/res/res_sorcery_config.c
+++ b/res/res_sorcery_config.c
@@ -65,6 +65,9 @@ struct sorcery_config {
 	/*! \brief Configuration is invalid in some way, force reload */
 	unsigned int configuration_invalid:1;
 
+	/*! \brief Configuration contains at least one object with dynamic contents */
+	unsigned int has_dynamic_contents:1;
+
 	/*! \brief Filename of the configuration file */
 	char filename[];
 };
@@ -313,12 +316,13 @@ static int sorcery_is_configuration_met(const struct ast_sorcery *sorcery, const
 static void sorcery_config_internal_load(void *data, const struct ast_sorcery *sorcery, const char *type, unsigned int reload)
 {
 	struct sorcery_config *config = data;
-	struct ast_flags flags = { reload && !config->configuration_invalid ? CONFIG_FLAG_FILEUNCHANGED : 0 };
+	struct ast_flags flags = { reload && !config->configuration_invalid && !config->has_dynamic_contents ? CONFIG_FLAG_FILEUNCHANGED : 0 };
 	struct ast_config *cfg = ast_config_load2(config->filename, config->uuid, flags);
 	struct ast_category *category = NULL;
 	RAII_VAR(struct ao2_container *, objects, NULL, ao2_cleanup);
 	const char *id = NULL;
 	unsigned int buckets = 0;
+	unsigned int has_dynamic_contents = 0;
 
 	if (!cfg) {
 		ast_log(LOG_ERROR, "Unable to load config file '%s'\n", config->filename);
@@ -430,9 +434,15 @@ static void sorcery_config_internal_load(void *data, const struct ast_sorcery *s
 			ast_log(LOG_NOTICE, "Retaining existing configuration for object of type '%s' with id '%s'\n", type, id);
 		}
 
+		/* We store the dynamic contents state until the end in case this reload or load
+		 * gets rolled back.
+		 */
+		has_dynamic_contents |= ast_sorcery_object_has_dynamic_contents(obj);
+
 		ao2_link(objects, obj);
 	}
 
+	config->has_dynamic_contents = has_dynamic_contents;
 	ao2_global_obj_replace_unref(config->objects, objects);
 	ast_config_destroy(cfg);
 }