diff --git a/codersdk/toolsdk/toolsdk_test.go b/codersdk/toolsdk/toolsdk_test.go
index a5d94e4306..37c4383b87 100644
--- a/codersdk/toolsdk/toolsdk_test.go
+++ b/codersdk/toolsdk/toolsdk_test.go
@@ -28,6 +28,7 @@ import (
 	"github.com/coder/coder/v2/agent/agenttest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbfake"
 	"github.com/coder/coder/v2/coderd/database/dbgen"
 	"github.com/coder/coder/v2/coderd/httpapi"
@@ -106,8 +107,9 @@ func TestTools(t *testing.T) {
 	})
 
 	t.Run("ReportTask", func(t *testing.T) {
+		ctx := testutil.Context(t, testutil.WaitShort)
 		tb, err := toolsdk.NewDeps(memberClient, toolsdk.WithTaskReporter(func(args toolsdk.ReportTaskArgs) error {
-			return agentClient.PatchAppStatus(setupCtx, agentsdk.PatchAppStatus{
+			return agentClient.PatchAppStatus(ctx, agentsdk.PatchAppStatus{
 				AppSlug: "some-agent-app",
 				Message: args.Summary,
 				URI:     args.Link,
@@ -1393,7 +1395,17 @@ func TestTools(t *testing.T) {
 		task := ws.Task
 
 		_ = agenttest.New(t, client.URL, ws.AgentToken)
-		coderdtest.NewWorkspaceAgentWaiter(t, client, ws.Workspace.ID).Wait()
+		coderdtest.NewWorkspaceAgentWaiter(t, client, ws.Workspace.ID).
+			WaitFor(coderdtest.AgentsReady)
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Ensure the app is healthy (required to send task input).
+		err = store.UpdateWorkspaceAppHealthByID(dbauthz.AsSystemRestricted(ctx), database.UpdateWorkspaceAppHealthByIDParams{
+			ID:     task.WorkspaceAppID.UUID,
+			Health: database.WorkspaceAppHealthHealthy,
+		})
+		require.NoError(t, err)
 
 		tests := []struct {
 			name  string
@@ -1454,8 +1466,6 @@ func TestTools(t *testing.T) {
 
 		for _, tt := range tests {
 			t.Run(tt.name, func(t *testing.T) {
-				t.Parallel()
-
 				tb, err := toolsdk.NewDeps(memberClient)
 				require.NoError(t, err)
 
@@ -1525,7 +1535,17 @@ func TestTools(t *testing.T) {
 		task := ws.Task
 
 		_ = agenttest.New(t, client.URL, ws.AgentToken)
-		coderdtest.NewWorkspaceAgentWaiter(t, client, ws.Workspace.ID).Wait()
+		coderdtest.NewWorkspaceAgentWaiter(t, client, ws.Workspace.ID).
+			WaitFor(coderdtest.AgentsReady)
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Ensure the app is healthy (required to read task logs).
+		err = store.UpdateWorkspaceAppHealthByID(dbauthz.AsSystemRestricted(ctx), database.UpdateWorkspaceAppHealthByIDParams{
+			ID:     task.WorkspaceAppID.UUID,
+			Health: database.WorkspaceAppHealthHealthy,
+		})
+		require.NoError(t, err)
 
 		tests := []struct {
 			name     string
@@ -1577,8 +1597,6 @@ func TestTools(t *testing.T) {
 
 		for _, tt := range tests {
 			t.Run(tt.name, func(t *testing.T) {
-				t.Parallel()
-
 				tb, err := toolsdk.NewDeps(memberClient)
 				require.NoError(t, err)