diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index cc05ecc73d3ef..b881e337906ba 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -1126,7 +1126,7 @@ func convertWorkspaceAgent(derpMap *tailcfg.DERPMap, coordinator tailnet.Coordin
 		ConnectionTimeoutSeconds:     dbAgent.ConnectionTimeoutSeconds,
 		TroubleshootingURL:           troubleshootingURL,
 		LifecycleState:               codersdk.WorkspaceAgentLifecycle(dbAgent.LifecycleState),
-		LoginBeforeReady:             dbAgent.StartupScriptBehavior == database.StartupScriptBehaviorNonBlocking,
+		LoginBeforeReady:             dbAgent.StartupScriptBehavior != database.StartupScriptBehaviorBlocking,
 		StartupScriptBehavior:        codersdk.WorkspaceAgentStartupScriptBehavior(dbAgent.StartupScriptBehavior),
 		StartupScriptTimeoutSeconds:  dbAgent.StartupScriptTimeoutSeconds,
 		ShutdownScript:               dbAgent.ShutdownScript.String,
diff --git a/codersdk/workspaceagents.go b/codersdk/workspaceagents.go
index dcede6a069f4f..b99185bd7cc8d 100644
--- a/codersdk/workspaceagents.go
+++ b/codersdk/workspaceagents.go
@@ -375,7 +375,18 @@ func (c *Client) WorkspaceAgent(ctx context.Context, id uuid.UUID) (WorkspaceAge
 		return WorkspaceAgent{}, ReadBodyAsError(res)
 	}
 	var workspaceAgent WorkspaceAgent
-	return workspaceAgent, json.NewDecoder(res.Body).Decode(&workspaceAgent)
+	err = json.NewDecoder(res.Body).Decode(&workspaceAgent)
+	if err != nil {
+		return WorkspaceAgent{}, err
+	}
+	// Backwards compatibility for cases where the API is older then the client.
+	if workspaceAgent.StartupScriptBehavior == "" {
+		workspaceAgent.StartupScriptBehavior = WorkspaceAgentStartupScriptBehaviorNonBlocking
+		if !workspaceAgent.LoginBeforeReady {
+			workspaceAgent.StartupScriptBehavior = WorkspaceAgentStartupScriptBehaviorBlocking
+		}
+	}
+	return workspaceAgent, nil
 }
 
 type IssueReconnectingPTYSignedTokenRequest struct {