diff --git a/cmd/mailroom/main.go b/cmd/mailroom/main.go
index a063f4cfa..f61055628 100644
--- a/cmd/mailroom/main.go
+++ b/cmd/mailroom/main.go
@@ -23,6 +23,7 @@ import (
 	_ "github.com/nyaruka/mailroom/core/tasks/groups"
 	_ "github.com/nyaruka/mailroom/core/tasks/interrupts"
 	_ "github.com/nyaruka/mailroom/core/tasks/ivr"
+	_ "github.com/nyaruka/mailroom/core/tasks/msgs"
 	_ "github.com/nyaruka/mailroom/core/tasks/schedules"
 	_ "github.com/nyaruka/mailroom/core/tasks/starts"
 	_ "github.com/nyaruka/mailroom/core/tasks/stats"
diff --git a/core/models/msgs.go b/core/models/msgs.go
index d5eea2cd5..b94e7f49a 100644
--- a/core/models/msgs.go
+++ b/core/models/msgs.go
@@ -9,6 +9,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/nyaruka/gocommon/dates"
 	"github.com/nyaruka/gocommon/gsm7"
 	"github.com/nyaruka/gocommon/urns"
 	"github.com/nyaruka/goflow/assets"
@@ -118,6 +119,7 @@ type Msg struct {
 		ContactURNID         *URNID             `db:"contact_urn_id"  json:"contact_urn_id"`
 		ResponseToID         MsgID              `db:"response_to_id"  json:"response_to_id"`
 		ResponseToExternalID null.String        `                     json:"response_to_external_id"`
+		IsResend             bool               `                     json:"is_resend,omitempty"`
 		URN                  urns.URN           `                     json:"urn"`
 		URNAuth              null.String        `                     json:"urn_auth,omitempty"`
 		OrgID                OrgID              `db:"org_id"          json:"org_id"`
@@ -164,6 +166,7 @@ func (m *Msg) OrgID() OrgID                     { return m.m.OrgID }
 func (m *Msg) TopupID() TopupID                 { return m.m.TopupID }
 func (m *Msg) ContactID() ContactID             { return m.m.ContactID }
 func (m *Msg) ContactURNID() *URNID             { return m.m.ContactURNID }
+func (m *Msg) IsResend() bool                   { return m.m.IsResend }
 
 func (m *Msg) SetTopup(topupID TopupID)               { m.m.TopupID = topupID }
 func (m *Msg) SetChannelID(channelID ChannelID)       { m.m.ChannelID = channelID }
@@ -382,6 +385,60 @@ func NewIncomingMsg(orgID OrgID, channel *Channel, contactID ContactID, in *flow
 	return msg
 }
 
+var loadMessagesSQL = `
+SELECT 
+	id,
+	broadcast_id,
+	uuid,
+	text,
+	created_on,
+	direction,
+	status,
+	visibility,
+	msg_count,
+	error_count,
+	next_attempt,
+	external_id,
+	attachments,
+	metadata,
+	channel_id,
+	connection_id,
+	contact_id,
+	contact_urn_id,
+	response_to_id,
+	org_id,
+	topup_id
+FROM
+	msgs_msg
+WHERE
+	org_id = $1 AND
+	direction = $2 AND
+	id = ANY($3)
+ORDER BY
+	id ASC`
+
+// LoadMessages loads the given messages for the passed in org
+func LoadMessages(ctx context.Context, db Queryer, orgID OrgID, direction MsgDirection, msgIDs []MsgID) ([]*Msg, error) {
+	rows, err := db.QueryxContext(ctx, loadMessagesSQL, orgID, direction, pq.Array(msgIDs))
+	if err != nil {
+		return nil, errors.Wrapf(err, "error querying msgs for org: %d", orgID)
+	}
+	defer rows.Close()
+
+	msgs := make([]*Msg, 0)
+	for rows.Next() {
+		msg := &Msg{}
+		err = rows.StructScan(&msg.m)
+		if err != nil {
+			return nil, errors.Wrap(err, "error scanning msg row")
+		}
+
+		msgs = append(msgs, msg)
+	}
+
+	return msgs, nil
+}
+
 // NormalizeAttachment will turn any relative URL in the passed in attachment and normalize it to
 // include the full host for attachment domains
 func NormalizeAttachment(attachment utils.Attachment) utils.Attachment {
@@ -949,6 +1006,73 @@ func CreateBroadcastMessages(ctx context.Context, db Queryer, rp *redis.Pool, oa
 	return msgs, nil
 }
 
+const updateMsgForResendingSQL = `
+	UPDATE
+		msgs_msg m
+	SET
+		channel_id = r.channel_id::int,
+		topup_id = r.topup_id::int,
+		status = 'P',
+		error_count = 0,
+		queued_on = r.queued_on::timestamp with time zone,
+		sent_on = NULL,
+		modified_on = NOW()
+	FROM (
+		VALUES(:id, :channel_id, :topup_id, :queued_on)
+	) AS
+		r(id, channel_id, topup_id, queued_on)
+	WHERE
+		m.id = r.id::bigint
+`
+
+// ResendMessages prepares messages for resending by reselecting a channel and marking them as PENDING
+func ResendMessages(ctx context.Context, db Queryer, rp *redis.Pool, oa *OrgAssets, msgs []*Msg) error {
+	channels := oa.SessionAssets().Channels()
+	resends := make([]interface{}, len(msgs))
+
+	for i, msg := range msgs {
+		// reselect channel for this message's URN
+		urn, err := URNForID(ctx, db, oa, *msg.ContactURNID())
+		if err != nil {
+			return errors.Wrap(err, "error loading URN")
+		}
+		contactURN, err := flows.ParseRawURN(channels, urn, assets.IgnoreMissing)
+		if err != nil {
+			return errors.Wrap(err, "error parsing URN")
+		}
+		ch := channels.GetForURN(contactURN, assets.ChannelRoleSend)
+		if ch != nil {
+			channel := oa.ChannelByUUID(ch.UUID())
+			msg.m.ChannelID = channel.ID()
+		} else {
+			msg.m.ChannelID = NilChannelID
+		}
+
+		// allocate a new topup for this message if org uses topups
+		msg.m.TopupID, err = AllocateTopups(ctx, db, rp, oa.Org(), 1)
+		if err != nil {
+			return errors.Wrapf(err, "error allocating topup for message resending")
+		}
+
+		// mark message as being a resend so it will be queued to courier as such
+		msg.m.Status = MsgStatusPending
+		msg.m.QueuedOn = dates.Now()
+		msg.m.SentOn = dates.ZeroDateTime
+		msg.m.ErrorCount = 0
+		msg.m.IsResend = true
+
+		resends[i] = msg.m
+	}
+
+	// update the messages in the database
+	err := BulkQuery(ctx, "updating messages for resending", db, updateMsgForResendingSQL, resends)
+	if err != nil {
+		return errors.Wrapf(err, "error updating messages for resending")
+	}
+
+	return nil
+}
+
 // MarkBroadcastSent marks the passed in broadcast as sent
 func MarkBroadcastSent(ctx context.Context, db Queryer, id BroadcastID) error {
 	// noop if it is a nil id
diff --git a/core/models/msgs_test.go b/core/models/msgs_test.go
index 6f0478c51..ab32a1396 100644
--- a/core/models/msgs_test.go
+++ b/core/models/msgs_test.go
@@ -5,6 +5,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/nyaruka/gocommon/dates"
 	"github.com/nyaruka/gocommon/urns"
 	"github.com/nyaruka/goflow/assets"
 	"github.com/nyaruka/goflow/flows"
@@ -147,6 +148,74 @@ func TestGetMessageIDFromUUID(t *testing.T) {
 	assert.Equal(t, models.MsgID(msgIn.ID()), msgID)
 }
 
+func TestLoadMessages(t *testing.T) {
+	ctx := testsuite.CTX()
+	db := testsuite.DB()
+	msgIn1 := testdata.InsertIncomingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "in 1")
+	msgOut1 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 1", []utils.Attachment{"image/jpeg:hi.jpg"})
+	msgOut2 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 2", nil)
+	msgOut3 := testdata.InsertOutgoingMsg(t, db, models.Org2, models.Org2FredID, models.Org2FredURN, models.Org2FredURNID, "out 3", nil)
+	testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "hi 3", nil)
+
+	ids := []models.MsgID{models.MsgID(msgIn1.ID()), models.MsgID(msgOut1.ID()), models.MsgID(msgOut2.ID()), models.MsgID(msgOut3.ID())}
+
+	msgs, err := models.LoadMessages(ctx, db, models.Org1, models.DirectionOut, ids)
+
+	// should only return the outgoing messages for this org
+	require.NoError(t, err)
+	assert.Equal(t, 2, len(msgs))
+	assert.Equal(t, "out 1", msgs[0].Text())
+	assert.Equal(t, []utils.Attachment{"image/jpeg:hi.jpg"}, msgs[0].Attachments())
+	assert.Equal(t, "out 2", msgs[1].Text())
+
+	msgs, err = models.LoadMessages(ctx, db, models.Org1, models.DirectionIn, ids)
+
+	// should only return the incoming message for this org
+	require.NoError(t, err)
+	assert.Equal(t, 1, len(msgs))
+	assert.Equal(t, "in 1", msgs[0].Text())
+}
+
+func TestResendMessages(t *testing.T) {
+	ctx := testsuite.CTX()
+	db := testsuite.DB()
+	rp := testsuite.RP()
+
+	db.MustExec(`DELETE FROM msgs_msg`)
+
+	oa, err := models.GetOrgAssets(ctx, db, models.Org1)
+	require.NoError(t, err)
+
+	msgOut1 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 1", nil)
+	msgOut2 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.BobID, models.BobURN, models.BobURNID, "out 2", nil)
+	testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 3", nil)
+
+	// make them look like failed messages
+	db.MustExec(`UPDATE msgs_msg SET status = 'F', sent_on = NOW(), error_count = 3`)
+
+	// give Bob's URN an affinity for the Vonage channel
+	db.MustExec(`UPDATE contacts_contacturn SET channel_id = $1 WHERE id = $2`, models.VonageChannelID, models.BobURNID)
+
+	msgs, err := models.LoadMessages(ctx, db, models.Org1, models.DirectionOut, []models.MsgID{models.MsgID(msgOut1.ID()), models.MsgID(msgOut2.ID())})
+	require.NoError(t, err)
+
+	now := dates.Now()
+
+	// resend both msgs
+	err = models.ResendMessages(ctx, db, rp, oa, msgs)
+	require.NoError(t, err)
+
+	// both messages should now have a channel, a topup and be marked for resending
+	assert.True(t, msgs[0].IsResend())
+	assert.Equal(t, models.TwilioChannelID, msgs[0].ChannelID())
+	assert.Equal(t, models.TopupID(1), msgs[0].TopupID())
+	assert.True(t, msgs[1].IsResend())
+	assert.Equal(t, models.VonageChannelID, msgs[1].ChannelID())
+	assert.Equal(t, models.TopupID(1), msgs[1].TopupID())
+
+	testsuite.AssertQueryCount(t, db, `SELECT count(*) FROM msgs_msg WHERE status = 'P' AND queued_on > $1 AND sent_on IS NULL`, []interface{}{now}, 2)
+}
+
 func TestNormalizeAttachment(t *testing.T) {
 	config.Mailroom.AttachmentDomain = "foo.bar.com"
 	defer func() { config.Mailroom.AttachmentDomain = "" }()
diff --git a/core/tasks/msgs/resend_msgs.go b/core/tasks/msgs/resend_msgs.go
new file mode 100644
index 000000000..2a705ef44
--- /dev/null
+++ b/core/tasks/msgs/resend_msgs.go
@@ -0,0 +1,53 @@
+package msgs
+
+import (
+	"context"
+	"time"
+
+	"github.com/nyaruka/mailroom"
+	"github.com/nyaruka/mailroom/core/models"
+	"github.com/nyaruka/mailroom/core/msgio"
+	"github.com/nyaruka/mailroom/core/tasks"
+
+	"github.com/pkg/errors"
+)
+
+// TypeResendMsgs is the type of the resend messages task
+const TypeResendMsgs = "resend_msgs"
+
+func init() {
+	tasks.RegisterType(TypeResendMsgs, func() tasks.Task { return &ResendMsgsTask{} })
+}
+
+// ResendMsgsTask is our task for resending messages
+type ResendMsgsTask struct {
+	MsgIDs []models.MsgID `json:"msg_ids"`
+}
+
+// Timeout is the maximum amount of time the task can run for
+func (t *ResendMsgsTask) Timeout() time.Duration {
+	return time.Minute * 5
+}
+
+func (t *ResendMsgsTask) Perform(ctx context.Context, mr *mailroom.Mailroom, orgID models.OrgID) error {
+	db := mr.DB
+	rp := mr.RP
+
+	oa, err := models.GetOrgAssets(ctx, mr.DB, orgID)
+	if err != nil {
+		return errors.Wrap(err, "unable to load org")
+	}
+
+	msgs, err := models.LoadMessages(ctx, db, orgID, models.DirectionOut, t.MsgIDs)
+	if err != nil {
+		return errors.Wrap(err, "error loading messages to resend")
+	}
+
+	err = models.ResendMessages(ctx, db, rp, oa, msgs)
+	if err != nil {
+		return errors.Wrap(err, "error cloning messages")
+	}
+
+	msgio.SendMessages(ctx, db, rp, nil, msgs)
+	return nil
+}
diff --git a/core/tasks/msgs/resend_msgs_test.go b/core/tasks/msgs/resend_msgs_test.go
new file mode 100644
index 000000000..30fc7990b
--- /dev/null
+++ b/core/tasks/msgs/resend_msgs_test.go
@@ -0,0 +1,43 @@
+package msgs_test
+
+import (
+	"testing"
+
+	"github.com/nyaruka/goflow/utils"
+	"github.com/nyaruka/mailroom"
+	"github.com/nyaruka/mailroom/config"
+	"github.com/nyaruka/mailroom/core/models"
+	"github.com/nyaruka/mailroom/core/tasks/msgs"
+	"github.com/nyaruka/mailroom/testsuite"
+	"github.com/nyaruka/mailroom/testsuite/testdata"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestResendMsgs(t *testing.T) {
+	testsuite.Reset()
+	ctx := testsuite.CTX()
+	db := testsuite.DB()
+	mr := &mailroom.Mailroom{Config: config.Mailroom, DB: db, RP: testsuite.RP(), ElasticClient: nil}
+
+	msgOut1 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 1", []utils.Attachment{"image/jpeg:hi.jpg"})
+	msgOut2 := testdata.InsertOutgoingMsg(t, db, models.Org1, models.BobID, models.BobURN, models.BobURNID, "out 2", nil)
+	testdata.InsertOutgoingMsg(t, db, models.Org1, models.CathyID, models.CathyURN, models.CathyURNID, "out 3", nil)
+
+	db.MustExec(`UPDATE msgs_msg SET metadata = '{"topic":"cool-stuff"}' WHERE id = $1`, msgOut1.ID())
+
+	// create our task
+	task := &msgs.ResendMsgsTask{
+		MsgIDs: []models.MsgID{models.MsgID(msgOut1.ID()), models.MsgID(msgOut2.ID())},
+	}
+
+	// execute it
+	err := task.Perform(ctx, mr, models.Org1)
+	require.NoError(t, err)
+
+	// the two resent messages should now be pending and have a channel set
+	testsuite.AssertQueryCount(t, db,
+		`SELECT count(*) FROM msgs_msg WHERE status = 'P' AND channel_id IS NOT NULL AND id IN ($1, $2)`,
+		[]interface{}{msgOut1.ID(), msgOut2.ID()}, 2,
+	)
+}
diff --git a/testsuite/testdata/msgs.go b/testsuite/testdata/msgs.go
index f4fc62964..beb9e9112 100644
--- a/testsuite/testdata/msgs.go
+++ b/testsuite/testdata/msgs.go
@@ -3,9 +3,11 @@ package testdata
 import (
 	"testing"
 
+	"github.com/lib/pq"
 	"github.com/nyaruka/gocommon/urns"
 	"github.com/nyaruka/gocommon/uuids"
 	"github.com/nyaruka/goflow/flows"
+	"github.com/nyaruka/goflow/utils"
 	"github.com/nyaruka/mailroom/core/models"
 
 	"github.com/jmoiron/sqlx"
@@ -25,3 +27,17 @@ func InsertIncomingMsg(t *testing.T, db *sqlx.DB, orgID models.OrgID, contactID
 	msg.SetID(id)
 	return msg
 }
+
+// InsertOutgoingMsg inserts an outgoing message
+func InsertOutgoingMsg(t *testing.T, db *sqlx.DB, orgID models.OrgID, contactID models.ContactID, urn urns.URN, urnID models.URNID, text string, attachments []utils.Attachment) *flows.MsgOut {
+	msg := flows.NewMsgOut(urn, nil, text, nil, nil, nil, flows.NilMsgTopic)
+
+	var id flows.MsgID
+	err := db.Get(&id,
+		`INSERT INTO msgs_msg(uuid, text, attachments, created_on, direction, status, visibility, msg_count, error_count, next_attempt, contact_id, contact_urn_id, org_id)
+	  	 VALUES($1, $2, $3, NOW(), 'O', 'P', 'V', 1, 0, NOW(), $4, $5, $6) RETURNING id`, msg.UUID(), text, pq.Array(attachments), contactID, urnID, orgID)
+	require.NoError(t, err)
+
+	msg.SetID(id)
+	return msg
+}