diff --git a/.changelog/15908.txt b/.changelog/15908.txt
new file mode 100644
index 000000000..22508a1ba
--- /dev/null
+++ b/.changelog/15908.txt
@@ -0,0 +1,3 @@
+```release-note:improvement
+docs: link to an envoy troubleshooting doc when envoy bootstrap fails
+```
diff --git a/client/allocrunner/taskrunner/envoy_bootstrap_hook.go b/client/allocrunner/taskrunner/envoy_bootstrap_hook.go
index 0da4c3d0d..fd852a49a 100644
--- a/client/allocrunner/taskrunner/envoy_bootstrap_hook.go
+++ b/client/allocrunner/taskrunner/envoy_bootstrap_hook.go
@@ -43,6 +43,10 @@ const (
 	envoyBootstrapMaxJitter = 500 * time.Millisecond
 )
 
+var (
+	errEnvoyBootstrapError = errors.New("error creating bootstrap configuration for Connect proxy sidecar")
+)
+
 type consulTransportConfig struct {
 	HTTPAddr   string // required
 	Auth       string // optional, env CONSUL_HTTP_AUTH
@@ -373,7 +377,10 @@ func (h *envoyBootstrapHook) Prestart(ctx context.Context, req *ifs.TaskPrestart
 		// Wrap the last error from Consul and set that as our status.
 		_, recoverable := cmdErr.(*exec.ExitError)
 		return structs.NewRecoverableError(
-			fmt.Errorf("error creating bootstrap configuration for Connect proxy sidecar: %v", cmdErr),
+			fmt.Errorf("%w: %v; see: <https://www.nomadproject.io/s/envoy-bootstrap-error>",
+				errEnvoyBootstrapError,
+				cmdErr,
+			),
 			recoverable,
 		)
 	}
diff --git a/client/allocrunner/taskrunner/envoy_bootstrap_hook_test.go b/client/allocrunner/taskrunner/envoy_bootstrap_hook_test.go
index 4fcfb623b..344332960 100644
--- a/client/allocrunner/taskrunner/envoy_bootstrap_hook_test.go
+++ b/client/allocrunner/taskrunner/envoy_bootstrap_hook_test.go
@@ -672,7 +672,7 @@ func TestTaskRunner_EnvoyBootstrapHook_RecoverableError(t *testing.T) {
 
 	// Run the hook
 	err := h.Prestart(context.Background(), req, resp)
-	require.EqualError(t, err, "error creating bootstrap configuration for Connect proxy sidecar: exit status 1")
+	require.ErrorIs(t, err, errEnvoyBootstrapError)
 	require.True(t, structs.IsRecoverable(err))
 
 	// Assert it is not Done
@@ -760,7 +760,7 @@ func TestTaskRunner_EnvoyBootstrapHook_retryTimeout(t *testing.T) {
 
 	// Run the hook and get the error
 	err := h.Prestart(context.Background(), req, &resp)
-	require.EqualError(t, err, "error creating bootstrap configuration for Connect proxy sidecar: exit status 1")
+	require.ErrorIs(t, err, errEnvoyBootstrapError)
 
 	// Current time should be at least start time + total wait time
 	minimum := begin.Add(h.envoyBootstrapWaitTime)
diff --git a/nomad/structs/structs.go b/nomad/structs/structs.go
index eb05ade65..7f8c0cf9d 100644
--- a/nomad/structs/structs.go
+++ b/nomad/structs/structs.go
@@ -11906,6 +11906,7 @@ type KeyringRequest struct {
 type RecoverableError struct {
 	Err         string
 	Recoverable bool
+	wrapped     error
 }
 
 // NewRecoverableError is used to wrap an error and mark it as recoverable or
@@ -11918,6 +11919,7 @@ func NewRecoverableError(e error, recoverable bool) error {
 	return &RecoverableError{
 		Err:         e.Error(),
 		Recoverable: recoverable,
+		wrapped:     e,
 	}
 }
 
@@ -11940,6 +11942,10 @@ func (r *RecoverableError) IsUnrecoverable() bool {
 	return !r.Recoverable
 }
 
+func (r *RecoverableError) Unwrap() error {
+	return r.wrapped
+}
+
 // Recoverable is an interface for errors to implement to indicate whether or
 // not they are fatal or recoverable.
 type Recoverable interface {
diff --git a/website/content/docs/integrations/consul-connect.mdx b/website/content/docs/integrations/consul-connect.mdx
index 34fa55cde..a20efebb3 100644
--- a/website/content/docs/integrations/consul-connect.mdx
+++ b/website/content/docs/integrations/consul-connect.mdx
@@ -371,6 +371,32 @@ dashes (`-`) are converted to underscores (`_`) in environment variables so
 - Prior to Consul 1.9, the Envoy sidecar proxy will drop and stop accepting
   connections while the Nomad agent is restarting.
 
+## Troubleshooting
+
+If the sidecar service is not running correctly, you can investigate
+potential `envoy` failures in the following ways:
+
+* Task logs in the associated `connect-*` task
+* Task secrets (may contain sensitive information):
+  * envoy CLI command: `secrets/.envoy_bootstrap.cmd`
+  * environment variables: `secrets/.envoy_bootstrap.env`
+* An extra Allocation log file: `alloc/logs/envoy_bootstrap.stderr.0`
+
+For example, with an allocation ID starting with `b36a`:
+
+```shell-session
+nomad alloc status -short b36a  # to get the connect-* task name
+nomad alloc logs -task connect-proxy-count-api -stderr b36a
+nomad alloc exec -task connect-proxy-count-api b36a cat secrets/.envoy_bootstrap.cmd
+nomad alloc exec -task connect-proxy-count-api b36a cat secrets/.envoy_bootstrap.env
+nomad alloc fs b36a alloc/logs/envoy_bootstrap.stderr.0
+```
+
+Note: If the alloc is unable to start successfully, debugging files may
+only be accessible from the host filesystem. However, the sidecar task secrets
+directory may not be available in systems where it is mounted in a temporary
+filesystem.
+
 [count-dashboard]: /img/count-dashboard.png
 [consul_acl]: https://github.com/hashicorp/consul/issues/7414
 [gh-9907]: https://github.com/hashicorp/nomad/issues/9907