diff --git a/internal/daemon/controller/handlers/targets/target_service.go b/internal/daemon/controller/handlers/targets/target_service.go
index 5fe6d07607..7e6bb67d5b 100644
--- a/internal/daemon/controller/handlers/targets/target_service.go
+++ b/internal/daemon/controller/handlers/targets/target_service.go
@@ -40,6 +40,7 @@ import (
 	"github.com/hashicorp/boundary/internal/types/subtypes"
 	"github.com/hashicorp/boundary/sdk/pbs/controller/api/resources/scopes"
 	pb "github.com/hashicorp/boundary/sdk/pbs/controller/api/resources/targets"
+	fm "github.com/hashicorp/boundary/version"
 	"github.com/hashicorp/go-bexpr"
 	"github.com/hashicorp/go-secure-stdlib/strutil"
 	"github.com/mr-tron/base58"
@@ -984,6 +985,13 @@ func (s Service) AuthorizeSession(ctx context.Context, req *pbs.AuthorizeSession
 		}
 	}
 
+	// this is an edge case issue where the hostId cannot be empty when trying to execute an ssh connection
+	// on a tcp target type. By setting the hostId to the targetId value, this will enable support of previous
+	// boundary cli versions.
+	if fm.SupportsFeature(fm.Binary, fm.UseTargetIdForHostId) && t.GetAddress() != "" {
+		hostId = t.GetPublicId()
+	}
+
 	sad := &pb.SessionAuthorizationData{
 		SessionId:       sess.PublicId,
 		TargetId:        t.GetPublicId(),
diff --git a/version/feature_manager.go b/version/feature_manager.go
index 7066851930..76e83a603c 100644
--- a/version/feature_manager.go
+++ b/version/feature_manager.go
@@ -28,6 +28,7 @@ const (
 	MultiHopSessionFeature
 	IncludeStatusInCli
 	CredentialLibraryVaultSubtype
+	UseTargetIdForHostId
 )
 
 var featureMap map[Feature]MetadataConstraint
@@ -65,6 +66,15 @@ func init() {
 		MetaInfo:    []Metadata{OSS, HCP},
 		Constraints: mustNewConstraints("< 0.14.0"),
 	}
+
+	// UseTargetIdForHostId supports old CLI clients that are unaware of host-sourceless targets,
+	// this feature populates the target's public id into the AuthorizeSessionResponse
+	// and the SessionAuthroizationData so the CLI can properly build the ssh command
+	// when calling "boundary connect ssh..."
+	featureMap[UseTargetIdForHostId] = MetadataConstraint{
+		MetaInfo:    []Metadata{OSS, HCP},
+		Constraints: mustNewConstraints("< 0.14.0"),
+	}
 }
 
 func metadataStringToMetadata(m string) Metadata {