diff --git a/internal/cmd/commands/server/server.go b/internal/cmd/commands/server/server.go
index dd453d3da8..d70b72a4f1 100644
--- a/internal/cmd/commands/server/server.go
+++ b/internal/cmd/commands/server/server.go
@@ -32,6 +32,7 @@ import (
 	"github.com/hashicorp/go-secure-stdlib/mlock"
 	"github.com/hashicorp/go-secure-stdlib/parseutil"
 	"github.com/hashicorp/go-secure-stdlib/pluginutil/v2"
+	"github.com/hashicorp/go-uuid"
 	"github.com/mitchellh/cli"
 	"github.com/posener/complete"
 	"go.uber.org/atomic"
@@ -330,6 +331,14 @@ func (c *Command) Run(args []string) int {
 				}
 			}
 		}
+
+		if c.Config.HCPBClusterId != "" {
+			_, err := uuid.ParseUUID(c.Config.HCPBClusterId)
+			if err != nil {
+				c.UI.Error(fmt.Errorf("Invalid HCPB cluster id %q: %w", c.Config.HCPBClusterId, err).Error())
+				return base.CommandUserError
+			}
+		}
 	}
 	if err := c.SetupListeners(c.UI, c.Config.SharedConfig, []string{"api", "cluster", "proxy", "ops"}); err != nil {
 		c.UI.Error(err.Error())
diff --git a/internal/cmd/config/config.go b/internal/cmd/config/config.go
index 4d45c617ad..7e054b0821 100644
--- a/internal/cmd/config/config.go
+++ b/internal/cmd/config/config.go
@@ -124,6 +124,9 @@ type Config struct {
 
 	// Plugin-related options
 	Plugins Plugins `hcl:"plugins"`
+
+	// Internal field for use with HCP deployments. Used if controllers/ initial_upstreams is not set
+	HCPBClusterId string `hcl:"hcp_boundary_cluster_id"`
 }
 
 type Controller struct {
diff --git a/internal/daemon/worker/controller_connection.go b/internal/daemon/worker/controller_connection.go
index e75ac8a624..82e410e4ea 100644
--- a/internal/daemon/worker/controller_connection.go
+++ b/internal/daemon/worker/controller_connection.go
@@ -35,6 +35,8 @@ import (
 	"google.golang.org/protobuf/proto"
 )
 
+const hcpbUrlSuffix = ".proxy.boundary.hashicorp.cloud"
+
 // StartControllerConnections starts up the resolver and initiates controller
 // connection client creation
 func (w *Worker) StartControllerConnections() error {
@@ -57,7 +59,13 @@ func (w *Worker) StartControllerConnections() error {
 	}
 
 	if len(initialAddrs) == 0 {
-		return errors.New("no initial controller addresses found")
+		if w.conf.RawConfig.HCPBClusterId != "" {
+			clusterAddress := fmt.Sprintf("%s%s", w.conf.RawConfig.HCPBClusterId, hcpbUrlSuffix)
+			initialAddrs = append(initialAddrs, resolver.Address{Addr: clusterAddress})
+			event.WriteSysEvent(context.TODO(), op, fmt.Sprintf("Setting HCPB Cluster address %s as upstream address", clusterAddress))
+		} else {
+			return errors.New("no initial controller addresses found")
+		}
 	}
 
 	w.Resolver().InitialState(resolver.State{
@@ -101,8 +109,10 @@ func (w *Worker) controllerDialerFunc() func(context.Context, string) (net.Conn,
 			event.WriteError(ctx, op, err)
 		}
 
-		if !w.everAuthenticated.Load() && err == nil && conn != nil {
-			w.everAuthenticated.Store(true)
+		if err == nil && conn != nil {
+			if !w.everAuthenticated.Load() {
+				w.everAuthenticated.Store(true)
+			}
 			event.WriteSysEvent(ctx, op, "worker has successfully authenticated")
 		}
 
diff --git a/internal/daemon/worker/status.go b/internal/daemon/worker/status.go
index 9891fe924c..89840a3aa7 100644
--- a/internal/daemon/worker/status.go
+++ b/internal/daemon/worker/status.go
@@ -3,21 +3,23 @@ package worker
 import (
 	"context"
 	"errors"
+	"fmt"
 	"math/rand"
 	"time"
 
-	"github.com/hashicorp/boundary/internal/servers"
-
 	"github.com/hashicorp/boundary/internal/daemon/worker/common"
 	"github.com/hashicorp/boundary/internal/daemon/worker/session"
 	pbs "github.com/hashicorp/boundary/internal/gen/controller/servers/services"
 	"github.com/hashicorp/boundary/internal/observability/event"
+	"github.com/hashicorp/boundary/internal/servers"
+	"github.com/hashicorp/go-secure-stdlib/strutil"
 	"google.golang.org/grpc/resolver"
 )
 
 type LastStatusInformation struct {
 	*pbs.StatusResponse
-	StatusTime time.Time
+	StatusTime              time.Time
+	LastCalculatedUpstreams []string
 }
 
 func (w *Worker) startStatusTicking(cancelCtx context.Context) {
@@ -199,14 +201,26 @@ func (w *Worker) sendWorkerStatus(cancelCtx context.Context) {
 	} else {
 		w.updateTags.Store(false)
 		// This may be nil if we are in a multiple hop scenario
+		var addrs []resolver.Address
+		var newUpstreams []string
 		if len(result.CalculatedUpstreams) > 0 {
-			addrs := make([]resolver.Address, 0, len(result.CalculatedUpstreams))
+			addrs = make([]resolver.Address, 0, len(result.CalculatedUpstreams))
 			for _, v := range result.CalculatedUpstreams {
 				addrs = append(addrs, resolver.Address{Addr: v.Address})
+				newUpstreams = append(newUpstreams, v.Address)
+			}
+			lastStatus := w.lastStatusSuccess.Load().(*LastStatusInformation)
+			// Compare upstreams; update resolver if there is a difference, and emit an event with old and new addresses
+			if lastStatus != nil && !strutil.EquivalentSlices(lastStatus.LastCalculatedUpstreams, newUpstreams) {
+				upstreamsMessage := fmt.Sprintf("Upstreams has changed; old upstreams were: %s, new upstreams are: %s", lastStatus.LastCalculatedUpstreams, newUpstreams)
+				event.WriteSysEvent(context.TODO(), op, upstreamsMessage)
+				w.Resolver().UpdateState(resolver.State{Addresses: addrs})
+			} else if lastStatus == nil {
+				w.Resolver().UpdateState(resolver.State{Addresses: addrs})
+				event.WriteSysEvent(context.TODO(), op, fmt.Sprintf("Upstreams after first status set to: %s", newUpstreams))
 			}
-			w.Resolver().UpdateState(resolver.State{Addresses: addrs})
 		}
-		w.lastStatusSuccess.Store(&LastStatusInformation{StatusResponse: result, StatusTime: time.Now()})
+		w.lastStatusSuccess.Store(&LastStatusInformation{StatusResponse: result, StatusTime: time.Now(), LastCalculatedUpstreams: newUpstreams})
 
 		for _, request := range result.GetJobsRequests() {
 			switch request.GetRequestType() {