diff --git a/api/proxy/option.go b/api/proxy/option.go
index d3aa24c5b0..3f37d89c33 100644
--- a/api/proxy/option.go
+++ b/api/proxy/option.go
@@ -9,6 +9,7 @@ import (
 	"net/netip"
 	"time"
 
+	"github.com/hashicorp/boundary/api"
 	"github.com/hashicorp/boundary/api/targets"
 )
 
@@ -37,6 +38,7 @@ type Options struct {
 	WithSessionAuthorizationData *targets.SessionAuthorizationData
 	WithSkipSessionTeardown      bool
 	withSessionTeardownTimeout   time.Duration
+	withApiClient                *api.Client
 }
 
 // Option is a function that takes in an options struct and sets values or
@@ -129,3 +131,14 @@ func WithSessionTeardownTimeout(with time.Duration) Option {
 		return nil
 	}
 }
+
+// WithApiClient provides an optional Boundary API client
+// Experimental: It is unclear whether the current usage of this option is the
+// approach that we want to take in the long term. This may be removed at any
+// point going forward.
+func WithApiClient(with *api.Client) Option {
+	return func(o *Options) error {
+		o.withApiClient = with
+		return nil
+	}
+}
diff --git a/api/proxy/option_test.go b/api/proxy/option_test.go
index 6b7f0a0d9b..8525010507 100644
--- a/api/proxy/option_test.go
+++ b/api/proxy/option_test.go
@@ -9,6 +9,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/hashicorp/boundary/api"
 	"github.com/hashicorp/boundary/api/targets"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -96,4 +97,15 @@ func Test_GetOpts(t *testing.T) {
 		require.NoError(t, err)
 		assert.Equal(3*time.Millisecond, opts.withSessionTeardownTimeout)
 	})
+	t.Run("withSessionsClient", func(t *testing.T) {
+		assert := assert.New(t)
+		opts, err := getOpts()
+		require.NoError(t, err)
+		assert.Nil(opts.withApiClient)
+		client, err := api.NewClient(nil)
+		require.NoError(t, err)
+		opts, err = getOpts(WithApiClient(client))
+		require.NoError(t, err)
+		assert.Equal(client, opts.withApiClient)
+	})
 }
diff --git a/api/proxy/proxy.go b/api/proxy/proxy.go
index 3e26da7f04..789dbfccf3 100644
--- a/api/proxy/proxy.go
+++ b/api/proxy/proxy.go
@@ -15,6 +15,8 @@ import (
 	"sync/atomic"
 	"time"
 
+	"github.com/hashicorp/boundary/api"
+	"github.com/hashicorp/boundary/api/sessions"
 	"github.com/hashicorp/boundary/api/targets"
 	cleanhttp "github.com/hashicorp/go-cleanhttp"
 	"github.com/hashicorp/go-secure-stdlib/base62"
@@ -37,6 +39,7 @@ type ClientProxy struct {
 	connectionsLeft         *atomic.Int32
 	connsLeftCh             chan int32
 	callerConnectionsLeftCh chan int32
+	apiClient               *api.Client
 	sessionAuthzData        *targets.SessionAuthorizationData
 	createTime              time.Time
 	expiration              time.Time
@@ -97,6 +100,7 @@ func New(ctx context.Context, authzToken string, opt ...Option) (*ClientProxy, e
 		callerConnectionsLeftCh: opts.WithConnectionsLeftCh,
 		started:                 new(atomic.Bool),
 		skipSessionTeardown:     opts.WithSkipSessionTeardown,
+		apiClient:               opts.withApiClient,
 	}
 
 	if opts.WithListener != nil {
@@ -260,6 +264,27 @@ func (p *ClientProxy) Start(opt ...Option) (retErr error) {
 					p.cancel()
 					return
 				}
+
+				// TODO: Determine if this is useful or if there is a better approach
+				// that we may use in the long term.
+				if p.apiClient != nil {
+					// If we can tell that the session for the connection we just
+					// closed is terminated, we can close the listener, otherwise
+					// might as well leave it open so the next connection can be
+					// tried.
+					sess, err := sessions.NewClient(p.apiClient).Read(p.ctx, p.sessionAuthzData.SessionId)
+					if err != nil || sess == nil || sess.Item == nil || sess.Item.TerminationReason == "" {
+						return
+					}
+
+					// We got a valid session response for the session we just
+					// closed a connection for. Since there is a termination reason
+					// we can treat the session as being terminated so no more
+					// connections will be able to be established.
+					fin <- fmt.Errorf("session no longer active")
+					listenerCloseFunc()
+					p.cancel()
+				}
 			}()
 		}
 	}()