diff --git a/NEXT_CHANGELOG.md b/NEXT_CHANGELOG.md
index eb422ac238a..cc0cd0c73bf 100644
--- a/NEXT_CHANGELOG.md
+++ b/NEXT_CHANGELOG.md
@@ -7,6 +7,7 @@
 ### CLI
 
 ### Bundles
+* `bundle validate` now warns when a job defines a `continuous` block without `continuous.task_retry_mode`, since it defaults to `NEVER` and the continuous job's tasks are not retried on failure ([#5691](https://github.com/databricks/cli/pull/5691)).
 * Add documentation for the common bundle resource fields `permissions`, `lifecycle`, and `grants` in the JSON schema, so they surface in editor completions and the docs.
 * `bundle run` now prints the modern job run URL (`/jobs/<id>/runs/<id>`) so that non-admin users permitted to view the run are taken to the run instead of the workspace homepage.
 * References to a registered model's `registered_model_id` now resolve under the direct engine, matching Terraform behavior ([#5621](https://github.com/databricks/cli/pull/5621)).
diff --git a/acceptance/bundle/validate/continuous_task_retry_mode/databricks.yml b/acceptance/bundle/validate/continuous_task_retry_mode/databricks.yml
new file mode 100644
index 00000000000..edb0de3f531
--- /dev/null
+++ b/acceptance/bundle/validate/continuous_task_retry_mode/databricks.yml
@@ -0,0 +1,25 @@
+bundle:
+  name: test-bundle
+
+resources:
+  jobs:
+    # Continuous job without task_retry_mode: should warn (defaults to NEVER).
+    continuous_no_retry:
+      name: continuous_no_retry
+      continuous:
+        pause_status: UNPAUSED
+      tasks:
+        - task_key: run_task
+          run_job_task:
+            job_id: 1234
+
+    # Continuous job with task_retry_mode set: should not warn.
+    continuous_with_retry:
+      name: continuous_with_retry
+      continuous:
+        pause_status: UNPAUSED
+        task_retry_mode: ON_FAILURE
+      tasks:
+        - task_key: run_task
+          run_job_task:
+            job_id: 1234
diff --git a/acceptance/bundle/validate/continuous_task_retry_mode/script b/acceptance/bundle/validate/continuous_task_retry_mode/script
new file mode 100644
index 00000000000..5350876150f
--- /dev/null
+++ b/acceptance/bundle/validate/continuous_task_retry_mode/script
@@ -0,0 +1 @@
+trace $CLI bundle validate
diff --git a/bundle/config/validate/continuous_task_retry_mode.go b/bundle/config/validate/continuous_task_retry_mode.go
new file mode 100644
index 00000000000..e0297608ecc
--- /dev/null
+++ b/bundle/config/validate/continuous_task_retry_mode.go
@@ -0,0 +1,56 @@
+package validate
+
+import (
+	"context"
+
+	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/libs/diag"
+	"github.com/databricks/cli/libs/dyn"
+	"github.com/databricks/cli/libs/log"
+)
+
+// ContinuousTaskRetryMode warns when a continuous job does not set task_retry_mode.
+// task_retry_mode defaults to NEVER, so the tasks of a continuous job are not
+// retried on failure unless it is explicitly set to ON_FAILURE.
+func ContinuousTaskRetryMode() bundle.ReadOnlyMutator {
+	return &continuousTaskRetryMode{}
+}
+
+type continuousTaskRetryMode struct{ bundle.RO }
+
+func (v *continuousTaskRetryMode) Name() string {
+	return "validate:continuous_task_retry_mode"
+}
+
+const continuousTaskRetryWarningSummary = "Continuous job does not set task_retry_mode"
+
+const continuousTaskRetryWarningDetail = `task_retry_mode is not set on this continuous job, so it defaults to NEVER and the job's tasks are not retried on failure.
+Set continuous.task_retry_mode to ON_FAILURE to enable task-level retries, or to NEVER to silence this warning.`
+
+func (v *continuousTaskRetryMode) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagnostics {
+	diags := diag.Diagnostics{}
+
+	pattern := dyn.NewPattern(dyn.Key("resources"), dyn.Key("jobs"), dyn.AnyKey(), dyn.Key("continuous"))
+
+	_, err := dyn.MapByPattern(b.Config.Value(), pattern, func(p dyn.Path, continuous dyn.Value) (dyn.Value, error) {
+		// An explicit task_retry_mode (NEVER or ON_FAILURE) is a deliberate
+		// choice, so we don't warn.
+		if continuous.Get("task_retry_mode").IsValid() {
+			return continuous, nil
+		}
+
+		diags = append(diags, diag.Diagnostic{
+			Severity:  diag.Warning,
+			Summary:   continuousTaskRetryWarningSummary,
+			Detail:    continuousTaskRetryWarningDetail,
+			Locations: continuous.Locations(),
+			Paths:     []dyn.Path{p},
+		})
+		return continuous, nil
+	})
+	if err != nil {
+		log.Debugf(ctx, "Error while applying continuous task retry mode validation: %s", err)
+	}
+
+	return diags
+}
diff --git a/bundle/config/validate/continuous_task_retry_mode_test.go b/bundle/config/validate/continuous_task_retry_mode_test.go
new file mode 100644
index 00000000000..9eac010733b
--- /dev/null
+++ b/bundle/config/validate/continuous_task_retry_mode_test.go
@@ -0,0 +1,98 @@
+package validate
+
+import (
+	"testing"
+
+	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/bundle/config"
+	"github.com/databricks/cli/bundle/config/resources"
+	"github.com/databricks/cli/bundle/internal/bundletest"
+	"github.com/databricks/cli/libs/diag"
+	"github.com/databricks/cli/libs/dyn"
+	"github.com/databricks/databricks-sdk-go/service/jobs"
+	"github.com/stretchr/testify/assert"
+)
+
+func TestContinuousTaskRetryModeWarnsWhenUnset(t *testing.T) {
+	ctx := t.Context()
+
+	b := &bundle.Bundle{
+		Config: config.Root{
+			Resources: config.Resources{
+				Jobs: map[string]*resources.Job{
+					"foo": {
+						JobSettings: jobs.JobSettings{
+							Continuous: &jobs.Continuous{},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	bundletest.SetLocation(b, "resources.jobs.foo.continuous", []dyn.Location{{File: "a.yml", Line: 1, Column: 1}})
+
+	diags := ContinuousTaskRetryMode().Apply(ctx, b)
+	assert.Equal(t, diag.Diagnostics{
+		{
+			Severity:  diag.Warning,
+			Summary:   continuousTaskRetryWarningSummary,
+			Detail:    continuousTaskRetryWarningDetail,
+			Locations: []dyn.Location{{File: "a.yml", Line: 1, Column: 1}},
+			Paths:     []dyn.Path{dyn.MustPathFromString("resources.jobs.foo.continuous")},
+		},
+	}, diags)
+}
+
+func TestContinuousTaskRetryModeNoWarningWhenSet(t *testing.T) {
+	ctx := t.Context()
+
+	b := &bundle.Bundle{
+		Config: config.Root{
+			Resources: config.Resources{
+				Jobs: map[string]*resources.Job{
+					"foo": {
+						JobSettings: jobs.JobSettings{
+							Continuous: &jobs.Continuous{
+								TaskRetryMode: jobs.TaskRetryModeOnFailure,
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	bundletest.SetLocation(b, "resources.jobs.foo.continuous", []dyn.Location{{File: "a.yml", Line: 1, Column: 1}})
+
+	diags := ContinuousTaskRetryMode().Apply(ctx, b)
+	assert.Empty(t, diags)
+}
+
+func TestContinuousTaskRetryModeNoWarningWithoutContinuous(t *testing.T) {
+	ctx := t.Context()
+
+	b := &bundle.Bundle{
+		Config: config.Root{
+			Resources: config.Resources{
+				Jobs: map[string]*resources.Job{
+					"foo": {
+						JobSettings: jobs.JobSettings{
+							Tasks: []jobs.Task{
+								{
+									TaskKey:      "my_task",
+									NotebookTask: &jobs.NotebookTask{},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	bundletest.SetLocation(b, "resources.jobs.foo", []dyn.Location{{File: "a.yml", Line: 1, Column: 1}})
+
+	diags := ContinuousTaskRetryMode().Apply(ctx, b)
+	assert.Empty(t, diags)
+}
diff --git a/bundle/config/validate/fast_validate.go b/bundle/config/validate/fast_validate.go
index d01eb8c1491..2ca7dbd6426 100644
--- a/bundle/config/validate/fast_validate.go
+++ b/bundle/config/validate/fast_validate.go
@@ -29,6 +29,7 @@ func (f *fastValidate) Apply(ctx context.Context, rb *bundle.Bundle) diag.Diagno
 		// Fast mutators with only in-memory checks
 		JobClusterKeyDefined(),
 		JobTaskClusterSpec(),
+		ContinuousTaskRetryMode(),
 
 		// Blocking mutators. Deployments will fail if these checks fail.
 		ValidateArtifactPath(),