diff --git a/contrib/ast-db-manage/config/versions/e658c26033ca_create_history_info_flag.py b/contrib/ast-db-manage/config/versions/e658c26033ca_create_history_info_flag.py
new file mode 100644
index 0000000000000000000000000000000000000000..fa3d4921f560ac2671ca03221cc7e7253dbb7dc9
--- /dev/null
+++ b/contrib/ast-db-manage/config/versions/e658c26033ca_create_history_info_flag.py
@@ -0,0 +1,38 @@
+"""create history info flag
+
+Revision ID: e658c26033ca
+Revises: 1ae0609b6646
+Create Date: 2020-08-13 10:53:21.032591
+
+"""
+
+# revision identifiers, used by Alembic.
+revision = 'e658c26033ca'
+down_revision = '1ae0609b6646'
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects.postgresql import ENUM
+
+AST_BOOL_NAME = 'ast_bool_values'
+# We'll just ignore the n/y and f/t abbreviations as Asterisk does not write
+# those aliases.
+AST_BOOL_VALUES = [ '0', '1',
+                    'off', 'on',
+                    'false', 'true',
+                    'no', 'yes' ]
+
+def upgrade():
+    ############################# Enums ##############################
+
+    # ast_bool_values has already been created, so use postgres enum object
+    # type to get around "already created" issue - works okay with mysql
+    ast_bool_values = ENUM(*AST_BOOL_VALUES, name=AST_BOOL_NAME, create_type=False)
+
+    op.add_column('ps_endpoints', sa.Column('send_history_info', ast_bool_values))
+
+
+def downgrade():
+    if op.get_context().bind.dialect.name == 'mssql':
+        op.drop_constraint('ck_ps_endpoints_send_history_info_ast_bool_values','ps_endpoints')
+    op.drop_column('ps_endpoints', 'send_history_info')
diff --git a/include/asterisk/res_pjsip.h b/include/asterisk/res_pjsip.h
index 48da005875a889913140fcceae89a20f001a5950..ddcf02fac2c65d8efa85233dfea07bf73707e907 100644
--- a/include/asterisk/res_pjsip.h
+++ b/include/asterisk/res_pjsip.h
@@ -648,6 +648,8 @@ struct ast_sip_endpoint_id_configuration {
 	unsigned int send_connected_line;
 	/*! When performing connected line update, which method should be used */
 	enum ast_sip_session_refresh_method refresh_method;
+	/*! Do we add History-Info headers to applicable outgoing requests/responses? */
+	unsigned int send_history_info;
 };
 
 /*!
diff --git a/res/res_pjsip.c b/res/res_pjsip.c
index d7655adde29ce77b65505b9c70ac12b859a761f1..9d3a6c28b28749b5bcc64e746af796c86e4eb448 100644
--- a/res/res_pjsip.c
+++ b/res/res_pjsip.c
@@ -659,6 +659,10 @@
 					<synopsis>Send the Diversion header, conveying the diversion
 					information to the called user agent</synopsis>
 				</configOption>
+				<configOption name="send_history_info" default="no">
+					<synopsis>Send the History-Info header, conveying the diversion
+					information to the called and calling user agents</synopsis>
+				</configOption>
 				<configOption name="send_pai" default="no">
 					<synopsis>Send the P-Asserted-Identity header</synopsis>
 				</configOption>
diff --git a/res/res_pjsip/pjsip_configuration.c b/res/res_pjsip/pjsip_configuration.c
index b23de7ed930e730b653dfb321c4a290cc71a0b7a..344f3191046f58cf4b2402299a5e6b9143d77872 100644
--- a/res/res_pjsip/pjsip_configuration.c
+++ b/res/res_pjsip/pjsip_configuration.c
@@ -2051,6 +2051,7 @@ int ast_res_pjsip_initialize_configuration(void)
 	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "send_rpid", "no", OPT_BOOL_T, 1, FLDSET(struct ast_sip_endpoint, id.send_rpid));
 	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "rpid_immediate", "no", OPT_BOOL_T, 1, FLDSET(struct ast_sip_endpoint, id.rpid_immediate));
 	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "send_diversion", "yes", OPT_BOOL_T, 1, FLDSET(struct ast_sip_endpoint, id.send_diversion));
+	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "send_history_info", "no", OPT_BOOL_T, 1, FLDSET(struct ast_sip_endpoint, id.send_history_info));
 	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "mailboxes", "", OPT_STRINGFIELD_T, 0, STRFLDSET(struct ast_sip_endpoint, subscription.mwi.mailboxes));
 	ast_sorcery_object_field_register_custom(sip_sorcery, "endpoint", "voicemail_extension", "", voicemail_extension_handler, voicemail_extension_to_str, NULL, 0, 0);
 	ast_sorcery_object_field_register(sip_sorcery, "endpoint", "aggregate_mwi", "yes", OPT_BOOL_T, 1, FLDSET(struct ast_sip_endpoint, subscription.mwi.aggregate));
diff --git a/res/res_pjsip_diversion.c b/res/res_pjsip_diversion.c
index 3f7487104d2b1732ba4c4fdc19258476db1709a1..9c69f5243b0d7de93b13402fb5d6b4bd0d406157 100644
--- a/res/res_pjsip_diversion.c
+++ b/res/res_pjsip_diversion.c
@@ -36,6 +36,8 @@
 #include "asterisk/strings.h"
 
 static const pj_str_t diversion_name = { "Diversion", 9 };
+static const pj_str_t history_info_name = { "History-Info", 12 };
+static pj_str_t HISTINFO_SUPPORTED_NAME = { "histinfo", 8 };
 
 /*!
  * \internal
@@ -80,22 +82,62 @@ static int sip_is_token(const char *str)
 static const struct reasons {
 	enum AST_REDIRECTING_REASON code;
 	const char *text;
+	const unsigned int cause;
 } reason_table[] = {
-	{ AST_REDIRECTING_REASON_UNKNOWN, "unknown" },
-	{ AST_REDIRECTING_REASON_USER_BUSY, "user-busy" },
-	{ AST_REDIRECTING_REASON_NO_ANSWER, "no-answer" },
-	{ AST_REDIRECTING_REASON_UNAVAILABLE, "unavailable" },
-	{ AST_REDIRECTING_REASON_UNCONDITIONAL, "unconditional" },
-	{ AST_REDIRECTING_REASON_TIME_OF_DAY, "time-of-day" },
-	{ AST_REDIRECTING_REASON_DO_NOT_DISTURB, "do-not-disturb" },
-	{ AST_REDIRECTING_REASON_DEFLECTION, "deflection" },
-	{ AST_REDIRECTING_REASON_FOLLOW_ME, "follow-me" },
-	{ AST_REDIRECTING_REASON_OUT_OF_ORDER, "out-of-service" },
-	{ AST_REDIRECTING_REASON_AWAY, "away" },
-	{ AST_REDIRECTING_REASON_CALL_FWD_DTE, "cf_dte" },		/* Non-standard */
-	{ AST_REDIRECTING_REASON_SEND_TO_VM, "send_to_vm" },	/* Non-standard */
+	{ AST_REDIRECTING_REASON_UNKNOWN, "unknown", 404 },
+	{ AST_REDIRECTING_REASON_USER_BUSY, "user-busy", 486 },
+	{ AST_REDIRECTING_REASON_NO_ANSWER, "no-answer", 408 },
+	{ AST_REDIRECTING_REASON_UNAVAILABLE, "unavailable", 503 },
+	{ AST_REDIRECTING_REASON_UNCONDITIONAL, "unconditional", 302 },
+	{ AST_REDIRECTING_REASON_TIME_OF_DAY, "time-of-day", 404 },
+	{ AST_REDIRECTING_REASON_DO_NOT_DISTURB, "do-not-disturb", 404 },
+	{ AST_REDIRECTING_REASON_DEFLECTION, "deflection", 480 },
+	{ AST_REDIRECTING_REASON_FOLLOW_ME, "follow-me", 404 },
+	{ AST_REDIRECTING_REASON_OUT_OF_ORDER, "out-of-service", 404 },
+	{ AST_REDIRECTING_REASON_AWAY, "away", 404 },
+	{ AST_REDIRECTING_REASON_CALL_FWD_DTE, "cf_dte", 404 },		/* Non-standard */
+	{ AST_REDIRECTING_REASON_SEND_TO_VM, "send_to_vm", 404 },	/* Non-standard */
 };
 
+static enum AST_REDIRECTING_REASON cause_to_reason(const unsigned long cause) {
+	switch(cause) {
+		case 302:
+			return AST_REDIRECTING_REASON_UNCONDITIONAL;
+		case 486:
+			return AST_REDIRECTING_REASON_USER_BUSY;
+		case 408:
+			return AST_REDIRECTING_REASON_NO_ANSWER;
+		case 480:
+		case 487:
+			return AST_REDIRECTING_REASON_DEFLECTION;
+		case 503:
+			return AST_REDIRECTING_REASON_UNAVAILABLE;
+		default:
+			return AST_REDIRECTING_REASON_UNKNOWN;
+	}
+}
+
+static int add_supported(pjsip_tx_data *tdata)
+{
+	pjsip_supported_hdr *hdr;
+
+	hdr = pjsip_msg_find_hdr(tdata->msg, PJSIP_H_SUPPORTED, NULL);
+	if (!hdr) {
+		/* insert a new Supported header */
+		hdr = pjsip_supported_hdr_create(tdata->pool);
+		if (!hdr) {
+			return -1;
+		}
+
+		pjsip_msg_add_hdr(tdata->msg, (pjsip_hdr *)hdr);
+	}
+
+	/* add on to the existing Supported header */
+	pj_strassign(&hdr->values[hdr->count++], &HISTINFO_SUPPORTED_NAME);
+
+	return 0;
+}
+
 static const char *reason_code_to_str(const struct ast_party_redirecting_reason *reason)
 {
 	int idx;
@@ -116,6 +158,21 @@ static const char *reason_code_to_str(const struct ast_party_redirecting_reason
 	return "unknown";
 }
 
+static const unsigned int reason_code_to_cause(const struct ast_party_redirecting_reason *reason)
+{
+	int idx;
+	int code;
+
+	code = reason->code;
+	for (idx = 0; idx < ARRAY_LEN(reason_table); ++idx) {
+		if (code == reason_table[idx].code) {
+			return reason_table[idx].cause;
+		}
+	}
+
+	return 404;
+}
+
 static pjsip_fromto_hdr *get_diversion_header(pjsip_rx_data *rdata)
 {
 	static const pj_str_t from_name = { "From", 4 };
@@ -135,6 +192,61 @@ static pjsip_fromto_hdr *get_diversion_header(pjsip_rx_data *rdata)
 			       pj_strlen(&value), &size);
 }
 
+/* Asterisk keeps track of 2 things. The redirected from address and
+ * the redirected to address. If first=0 method will get the most recent
+ * redirection target for use as the redirected to address. If first=1
+ * then this method will get the original redirection target (index=1)
+ * for use as the redirected from address.
+ */
+static pjsip_fromto_hdr *get_history_info_header(pjsip_rx_data *rdata, const unsigned int first)
+{
+	static const pj_str_t from_name = { "From", 4 };
+	pjsip_fromto_hdr * result_hdr = NULL;
+
+	pjsip_generic_string_hdr *hdr = NULL;
+
+	hdr = pjsip_msg_find_hdr_by_name(rdata->msg_info.msg, &history_info_name, NULL);
+
+	if (!hdr) {
+		return NULL;
+	}
+
+	do {
+		static const pj_str_t index_name = { "index", 5 };
+		pj_str_t value;
+		int size;
+		pjsip_fromto_hdr * fromto_hdr = NULL;
+		pjsip_param * index = NULL;
+
+		pj_strdup_with_null(rdata->tp_info.pool, &value, &hdr->hvalue);
+
+		/* parse as a fromto header */
+		fromto_hdr =  pjsip_parse_hdr(rdata->tp_info.pool, &from_name, value.ptr,
+				       pj_strlen(&value), &size);
+
+		if (fromto_hdr == NULL) {
+			continue;
+		}
+
+		index = pjsip_param_find(&fromto_hdr->other_param, &index_name);
+
+		if (index) {
+			if (!pj_strcmp2(&index->value, "1")) {
+				if (!first) {
+					continue;
+				} else {
+					return fromto_hdr;
+				}
+			}
+		}
+
+		result_hdr = fromto_hdr;
+
+	} while ((hdr = pjsip_msg_find_hdr_by_name(rdata->msg_info.msg, &history_info_name, hdr->next)));
+
+	return result_hdr;
+}
+
 static void set_redirecting_value(char **dst, const pj_str_t *src)
 {
 	ast_free(*dst);
@@ -197,14 +309,36 @@ static void copy_redirecting_id(struct ast_party_id *dst, const struct ast_party
 	}
 }
 
-static void set_redirecting_reason(pjsip_fromto_hdr *hdr,
+static void set_redirecting_reason_by_cause(pjsip_name_addr *name_addr,
+				   struct ast_party_redirecting_reason *data)
+{
+	static const pj_str_t cause_name = { "cause", 5 };
+	pjsip_sip_uri *uri = pjsip_uri_get_uri(name_addr);
+	pjsip_param *cause = pjsip_param_find(&uri->other_param, &cause_name);
+	unsigned long cause_value;
+
+	if (!cause) {
+		return;
+	}
+
+	cause_value = pj_strtoul(&cause->value);
+
+	data->code = cause_to_reason(cause_value);
+	ast_free(data->str);
+	data->str = ast_strdup("");
+}
+
+static void set_redirecting_reason(pjsip_fromto_hdr *from_info, pjsip_name_addr *to_info,
 				   struct ast_party_redirecting_reason *data)
 {
 	static const pj_str_t reason_name = { "reason", 6 };
-	pjsip_param *reason = pjsip_param_find(&hdr->other_param, &reason_name);
+	pjsip_param *reason = pjsip_param_find(&from_info->other_param, &reason_name);
 	char *reason_str;
 
 	if (!reason) {
+		if (to_info) {
+			set_redirecting_reason_by_cause(to_info, data);
+		}
 		return;
 	}
 
@@ -246,12 +380,15 @@ static void set_redirecting(struct ast_sip_session *session,
 	if (from_info) {
 		set_redirecting_id((pjsip_name_addr*)from_info->uri,
 			&data.from, &update.from);
-		set_redirecting_reason(from_info, &data.reason);
+		set_redirecting_reason(from_info, to_info, &data.reason);
+		ast_set_party_id_all(&update.priv_to);
 	} else {
 		copy_redirecting_id(&data.from, &session->id, &update.from);
 	}
 
-	set_redirecting_id(to_info, &data.to, &update.to);
+	if (to_info) {
+		set_redirecting_id(to_info, &data.to, &update.to);
+	}
 
 	ast_set_party_id_all(&update.priv_orig);
 	ast_set_party_id_all(&update.priv_from);
@@ -273,6 +410,17 @@ static int diversion_incoming_request(struct ast_sip_session *session, pjsip_rx_
 	if (hdr) {
 		set_redirecting(session, hdr, (pjsip_name_addr*)
 				PJSIP_MSG_TO_HDR(rdata->msg_info.msg)->uri);
+	} else {
+		pjsip_fromto_hdr *history_info_to;
+		pjsip_fromto_hdr *history_info_from;
+		history_info_to  = get_history_info_header(rdata, 0);
+
+		if (history_info_to) {
+			/* If History-Info is present, then it will also include the original
+			   redirected-from in addition to the redirected-to */
+			history_info_from = get_history_info_header(rdata, 1);
+			set_redirecting(session, history_info_from, (pjsip_name_addr*)history_info_to->uri);
+		}
 	}
 
 	return 0;
@@ -285,6 +433,8 @@ static void diversion_incoming_response(struct ast_sip_session *session, pjsip_r
 
 	pjsip_status_line status = rdata->msg_info.msg->line.status;
 	pjsip_fromto_hdr *div_hdr;
+	pjsip_fromto_hdr *history_info_to;
+	pjsip_fromto_hdr *history_info_from;
 	pjsip_contact_hdr *contact_hdr;
 
 	if ((status.code != 302) && (status.code != 181)) {
@@ -292,15 +442,35 @@ static void diversion_incoming_response(struct ast_sip_session *session, pjsip_r
 	}
 
 	/* use the diversion header info if there is one. if not one then use the
-           session caller id info. if that doesn't exist use info from the To hdr*/
-	if (!(div_hdr = get_diversion_header(rdata)) && !session->id.number.valid) {
-		div_hdr = PJSIP_MSG_TO_HDR(rdata->msg_info.msg);
+	   the history-info, if that doesn't exist, use session caller id info. if
+	   that doesn't exist use info from the To hdr*/
+	if (!(div_hdr = get_diversion_header(rdata))) {
+		history_info_to  = get_history_info_header(rdata, 0);
+
+		if (history_info_to) {
+			/* If History-Info is present, then it will also include the original
+			   redirected-from in addition to the redirected-to */
+			history_info_from = get_history_info_header(rdata, 1);
+			set_redirecting(session, history_info_from, (pjsip_name_addr*)history_info_to->uri);
+			return;
+		}
+		if (!div_hdr && !session->id.number.valid) {
+			div_hdr = PJSIP_MSG_TO_HDR(rdata->msg_info.msg);
+		}
 	}
 
-	contact_hdr = pjsip_msg_find_hdr_by_names(rdata->msg_info.msg, &contact_name, &contact_name_s, NULL);
 
-	set_redirecting(session, div_hdr, contact_hdr ?	(pjsip_name_addr*)contact_hdr->uri :
-			(pjsip_name_addr*)PJSIP_MSG_FROM_HDR(rdata->msg_info.msg)->uri);
+	if (status.code == 302) {
+		/* With 302, Contact indicates the final destination and possibly Diversion indicates the hop before */
+		contact_hdr = pjsip_msg_find_hdr_by_names(rdata->msg_info.msg, &contact_name, &contact_name_s, NULL);
+
+		set_redirecting(session, div_hdr, contact_hdr ?	(pjsip_name_addr*)contact_hdr->uri :
+				(pjsip_name_addr*)PJSIP_MSG_FROM_HDR(rdata->msg_info.msg)->uri);
+	} else {
+		/* With 181, Diversion is non-standard, but if present indicates the new final destination, and To indicating the original */
+		set_redirecting(session, PJSIP_MSG_TO_HDR(rdata->msg_info.msg),
+				div_hdr ? (pjsip_name_addr*)div_hdr->uri : NULL);
+	}
 }
 
 /*!
@@ -312,6 +482,8 @@ static void diversion_incoming_response(struct ast_sip_session *session, pjsip_r
  */
 static void add_diversion_header(pjsip_tx_data *tdata, struct ast_party_redirecting *data)
 {
+	static const pj_str_t reason_name = { "reason", 6 };
+
 	pjsip_fromto_hdr *hdr;
 	pjsip_name_addr *name_addr;
 	pjsip_sip_uri *uri;
@@ -320,9 +492,17 @@ static void add_diversion_header(pjsip_tx_data *tdata, struct ast_party_redirect
 	const char *reason_str;
 	const char *quote_str;
 	char *reason_buf;
+	pjsip_uri *base;
+
+	struct ast_party_id *id = NULL;
+	if (tdata->msg->type == PJSIP_REQUEST_MSG) {
+		id = &data->from;
+	} else {
+		/* In responses indicate the new destination */
+		id = &data->to;
+	}
 
-	struct ast_party_id *id = &data->from;
-	pjsip_uri *base = PJSIP_MSG_FROM_HDR(tdata->msg)->uri;
+	base = PJSIP_MSG_FROM_HDR(tdata->msg)->uri;
 
 	if (!id->number.valid || ast_strlen_zero(id->number.str)) {
 		return;
@@ -339,7 +519,7 @@ static void add_diversion_header(pjsip_tx_data *tdata, struct ast_party_redirect
 	pj_strdup2(tdata->pool, &uri->user, id->number.str);
 
 	param = PJ_POOL_ALLOC_T(tdata->pool, pjsip_param);
-	param->name = pj_str("reason");
+	param->name = reason_name;
 
 	reason_str = reason_code_to_str(&data->reason);
 
@@ -361,14 +541,106 @@ static void add_diversion_header(pjsip_tx_data *tdata, struct ast_party_redirect
 	pjsip_msg_add_hdr(tdata->msg, (pjsip_hdr *)hdr);
 }
 
+/*!
+ * \internal
+ * \brief Adds history-info header information to an outbound SIP message
+ *
+ * \param tdata The outbound message
+ * \param data The redirecting data used to fill parts of the history-info header
+ */
+static void add_history_info_header(pjsip_tx_data *tdata, struct ast_party_redirecting *data)
+{
+	static const pj_str_t index_name = { "index", 5 };
+	static const pj_str_t cause_name = { "cause", 5 };
+	static const pj_str_t first_index = { "1", 1 };
+	static const pj_str_t last_index = { "1.1", 3 };
+
+	pjsip_fromto_hdr *hdr;
+	pjsip_name_addr *name_addr;
+	pjsip_sip_uri *uri;
+	pjsip_param *param;
+	pjsip_fromto_hdr *old_hdr;
+	unsigned int cause;
+	char *cause_buf;
+
+	struct ast_party_id *to = &data->to;
+	struct ast_party_id *from = &data->from;
+
+	pjsip_uri *base = PJSIP_MSG_TO_HDR(tdata->msg)->uri;
+
+
+	hdr = pjsip_from_hdr_create(tdata->pool);
+	hdr->type = PJSIP_H_OTHER;
+	hdr->sname = hdr->name = history_info_name;
+
+	name_addr = pjsip_uri_clone(tdata->pool, base);
+	uri = pjsip_uri_get_uri(name_addr->uri);
+
+	/* if no redirecting information, then TO is the original destination */
+	if (from->number.valid && !ast_strlen_zero(from->number.str)) {
+		pj_strdup2(tdata->pool, &name_addr->display, from->name.str);
+		pj_strdup2(tdata->pool, &uri->user, from->number.str);
+	}
+
+	param = PJ_POOL_ALLOC_T(tdata->pool, pjsip_param);
+	param->name = index_name;
+	param->value = first_index;
+
+
+	pj_list_insert_before(&hdr->other_param, param);
+	hdr->uri = (pjsip_uri *) name_addr;
+
+	while ((old_hdr = pjsip_msg_find_hdr_by_name(tdata->msg, &history_info_name, NULL)) != NULL) {
+		pj_list_erase(old_hdr);
+	}
+
+	pjsip_msg_add_hdr(tdata->msg, (pjsip_hdr *)hdr);
+
+	if (!to->number.valid || ast_strlen_zero(to->number.str)) {
+		return;
+	}
+
+	hdr = pjsip_from_hdr_create(tdata->pool);
+	hdr->type = PJSIP_H_OTHER;
+	hdr->sname = hdr->name = history_info_name;
+
+	name_addr = pjsip_uri_clone(tdata->pool, base);
+	uri = pjsip_uri_get_uri(name_addr->uri);
+
+	pj_strdup2(tdata->pool, &name_addr->display, to->name.str);
+	pj_strdup2(tdata->pool, &uri->user, to->number.str);
+
+	param = PJ_POOL_ALLOC_T(tdata->pool, pjsip_param);
+	param->name = index_name;
+	param->value = last_index;
+	pj_list_insert_before(&hdr->other_param, param);
+
+	param = PJ_POOL_ALLOC_T(tdata->pool, pjsip_param);
+	param->name = cause_name;
+	cause = reason_code_to_cause(&data->reason);
+	cause_buf = pj_pool_alloc(tdata->pool, 4);
+	snprintf(cause_buf, 4, "%ud", cause);
+	param->value = pj_str(cause_buf);
+	pj_list_insert_before(&uri->other_param, param);
+	hdr->uri = (pjsip_uri *) name_addr;
+
+	pjsip_msg_add_hdr(tdata->msg, (pjsip_hdr *)hdr);
+}
+
 static void get_redirecting_add_diversion(struct ast_sip_session *session, pjsip_tx_data *tdata)
 {
 	struct ast_party_redirecting *data;
 
+	add_supported(tdata);
+
 	if (session->channel && session->endpoint->id.send_diversion &&
 	    (data = ast_channel_redirecting(session->channel))->count) {
 		add_diversion_header(tdata, data);
 	}
+	if (session->channel && session->endpoint->id.send_history_info) {
+		data = ast_channel_redirecting(session->channel);
+		add_history_info_header(tdata, data);
+	}
 }
 
 /*!