diff --git a/docs/src/content/docs/workflows.md b/docs/src/content/docs/workflows.md
index 15b7c085..862aa5bb 100644
--- a/docs/src/content/docs/workflows.md
+++ b/docs/src/content/docs/workflows.md
@@ -354,7 +354,9 @@ For the trunk branch, `cascade branch-protection` emits the full JSON body to PU
 
 ## Rollback
 
-cascade generates a standalone `cascade-rollback.yaml` workflow whenever the manifest declares at least one environment. It re-deploys a prior version or SHA to a target environment, defaulting to the previous version (N-1). A read-only preflight resolves the target, the deploy stage re-runs the configured deploy callbacks keyed on the resolved SHA, and finalize writes the rolled-back state back to trunk.
+cascade generates a standalone `cascade-rollback.yaml` workflow whenever the manifest declares at least two environments. It re-deploys a prior version or SHA to a target environment, defaulting to the previous version (N-1). A read-only preflight resolves the target, the deploy stage re-runs the configured deploy callbacks keyed on the resolved SHA, and finalize writes the rolled-back state back to trunk.
+
+Rollback covers the promoted environments only. The first environment tracks trunk and is never promoted into, so it keeps no deploy history to roll back to: roll it forward by reverting the offending change on the trunk branch instead. The workflow dropdown offers only the promoted environments, and a rollback aimed at the first environment fails fast with that guidance.
 
 By default the workflow is triggered by manual dispatch only (`workflow_dispatch`).
 
diff --git a/e2e/harness/multistep.go b/e2e/harness/multistep.go
index 2afacd0c..a6eb92a8 100644
--- a/e2e/harness/multistep.go
+++ b/e2e/harness/multistep.go
@@ -212,7 +212,10 @@ type PromoteStep struct {
 // failure (for example a rollback whose preflight cannot resolve a target),
 // mirroring PromoteStep.ExpectFailure. ExpectSource, when non-empty, asserts the
 // resolved-target source label that the preflight job echoes to its job log
-// (one of "state", "previous-ring", or "git-history").
+// (one of "state", "previous-ring", or "git-history"). ExpectLog, when set
+// alongside ExpectFailure, asserts the failing run's logs contain the given
+// substring, so a scenario can prove the run failed for the expected reason (for
+// example the first-environment guard message) rather than an unrelated fault.
 type RollbackStep struct {
 	Environment   string `yaml:"environment"`
 	Target        string `yaml:"target,omitempty"`
@@ -220,6 +223,7 @@ type RollbackStep struct {
 	DryRun        bool   `yaml:"dry_run,omitempty"`
 	ExpectFailure bool   `yaml:"expect_failure,omitempty"`
 	ExpectSource  string `yaml:"expect_source,omitempty"`
+	ExpectLog     string `yaml:"expect_log,omitempty"`
 }
 
 // VerifyStep defines a verify action: a read-only `cascade verify` run in the
diff --git a/e2e/harness/rollback_actions.go b/e2e/harness/rollback_actions.go
index 5f51c34a..6e17b978 100644
--- a/e2e/harness/rollback_actions.go
+++ b/e2e/harness/rollback_actions.go
@@ -3,6 +3,7 @@ package harness
 import (
 	"context"
 	"fmt"
+	"strings"
 )
 
 // rollbackWorkflowPath is the generated rollback workflow's path inside the repo.
@@ -86,6 +87,13 @@ func (r *Runner) executeRollback(ctx context.Context, rollback *RollbackStep, co
 	// Handle expected failures (mirrors executePromote's ExpectFailure path).
 	if rollback.ExpectFailure {
 		if result.Conclusion == "failure" {
+			// When ExpectLog is set, assert the failure logs carry the expected
+			// marker so the scenario proves the run failed for the intended reason
+			// (for example the first-environment guard) and not an unrelated fault.
+			if rollback.ExpectLog != "" && !strings.Contains(result.Logs, rollback.ExpectLog) {
+				r.t.Logf("  Rollback workflow logs:\n%s", result.Logs)
+				return fmt.Errorf("rollback failed as expected but logs did not contain %q", rollback.ExpectLog)
+			}
 			r.t.Log("  Rollback: workflow failed as expected")
 			return nil
 		}
diff --git a/e2e/scenarios/rollback/rollback-first-env-guard.yaml b/e2e/scenarios/rollback/rollback-first-env-guard.yaml
new file mode 100644
index 00000000..c57daa79
--- /dev/null
+++ b/e2e/scenarios/rollback/rollback-first-env-guard.yaml
@@ -0,0 +1,123 @@
+name: "Rollback refuses the first environment, allows a promoted one"
+description: |
+  Proves the first-environment rollback guard end to end. The first environment
+  tracks trunk and is never promoted into, so it keeps no deploy-history ring to
+  resolve a prior target from. A rollback there must fail fast with an actionable
+  message rather than silently re-point at an empty or stale ring. A promoted
+  environment still rolls back normally.
+
+  dev is the first environment. prod is advanced through two published versions
+  so it has a real prior target. The scenario then dispatches two rollbacks:
+
+    1. Rollback dev (the first env): the preflight refuses it. The run concludes
+       in failure and its logs carry the guard message, asserted via expect_log.
+    2. Rollback prod (a promoted env): resolves N-1 from the previous-deploy ring,
+       re-deploys at that SHA, and lands prod back on the first version.
+
+config:
+  trunk_branch: main
+  environments: [dev, prod]
+  builds:
+    - name: app
+      workflow: build.yaml
+      triggers: ["src/**"]
+  deploys:
+    # Reusable deploy whose inner job echoes the resolved env/sha, so the deploy
+    # job runs observably under act without a checkout step. act keys it by the
+    # inner job id appdeploy, which the harness assertion targets.
+    - name: app
+      workflow: .github/workflows/deploy-app.yaml
+      triggers: ["**"]
+
+steps:
+  - name: "Commit the first version source"
+    action: commit
+    commit:
+      message: "feat: first version"
+      files:
+        src/app.go: |
+          package main
+          func main() {}
+        .github/workflows/deploy-app.yaml: |
+          name: deploy-app
+          on:
+            workflow_call:
+              inputs:
+                environment:
+                  required: false
+                  type: string
+                sha:
+                  required: false
+                  type: string
+          jobs:
+            appdeploy:
+              runs-on: ubuntu-latest
+              steps:
+                - run: echo "deployed env=${{ inputs.environment }} sha=${{ inputs.sha }}"
+
+  - name: "Orchestrate the first commit into dev"
+    action: orchestrate
+    expect:
+      state:
+        dev:
+          sha: commit1
+
+  - name: "Promote the first version from dev to prod (establishes the prior target)"
+    action: promote
+    promote:
+      mode: cascade
+      target: prod
+    expect:
+      state:
+        prod:
+          sha: commit1
+
+  - name: "Commit a second version source"
+    action: commit
+    commit:
+      message: "feat: second version"
+      files:
+        src/app.go: |
+          package main
+          func main() { _ = 2 }
+
+  - name: "Orchestrate the second commit into dev"
+    action: orchestrate
+    expect:
+      state:
+        dev:
+          sha: commit2
+
+  - name: "Promote the second version from dev to prod (advances past the prior target)"
+    action: promote
+    promote:
+      mode: cascade
+      target: prod
+    expect:
+      state:
+        prod:
+          sha: commit2
+
+  # Rollback the first environment: the preflight refuses it before resolving any
+  # target. The run concludes in failure and its logs carry the guard message.
+  - name: "Rollback dev (the first environment) fails fast with the guard message"
+    action: rollback
+    rollback:
+      environment: dev
+      expect_failure: true
+      expect_log: "is the first environment"
+
+  # Rollback a promoted environment: resolves N-1 from the previous-deploy ring,
+  # re-deploys at that SHA, and prod state lands back on commit1.
+  - name: "Rollback prod (a promoted environment) succeeds"
+    action: rollback
+    rollback:
+      environment: prod
+    expect:
+      state:
+        prod:
+          sha: commit1
+      jobs:
+        preflight: success
+        appdeploy: success
+        finalize: success
diff --git a/internal/generate/rollback.go b/internal/generate/rollback.go
index 095f6130..06a46d77 100644
--- a/internal/generate/rollback.go
+++ b/internal/generate/rollback.go
@@ -32,11 +32,14 @@ func NewRollbackGenerator(cfg *config.TrunkConfig, baseDir string) *RollbackGene
 	}
 }
 
-// Enabled reports whether the rollback workflow should be emitted. It is emitted
-// when the manifest declares at least one environment, since a rollback re-points
-// an environment at a prior deployment.
+// Enabled reports whether the rollback workflow should be emitted. It requires
+// at least two environments: a rollback re-points a promoted environment at a
+// prior deployment, and the first environment tracks trunk (it is never promoted
+// into, so it has no rollback history and reverts via a merge to trunk instead).
+// A single-environment project therefore has no rollbackable environment, so the
+// workflow is not emitted, mirroring the hotfix generator.
 func (g *RollbackGenerator) Enabled() bool {
-	return g.config != nil && len(g.config.Environments) >= 1
+	return g.config != nil && len(g.config.Environments) >= 2
 }
 
 // dispatchTrigger returns the configured opt-in repository_dispatch trigger, or
@@ -128,14 +131,21 @@ func (g *RollbackGenerator) writeTriggers(sb *strings.Builder) {
 	sb.WriteString("  workflow_dispatch:\n")
 	sb.WriteString("    inputs:\n")
 
-	// environment: enumerate the configured environments as a choice so the
-	// operator picks from the declared set rather than free-typing.
+	// environment: enumerate the promoted environments as a choice so the operator
+	// picks from the declared set rather than free-typing. The first environment
+	// is excluded: it tracks trunk and is refused by the rollback runtime guard, so
+	// offering it in the dropdown would only surface a guaranteed failure. Enabled
+	// gates emission on at least two environments, so Environments[1:] is non-empty.
 	sb.WriteString("      environment:\n")
 	sb.WriteString("        description: 'Environment to roll back'\n")
 	sb.WriteString("        required: true\n")
 	sb.WriteString("        type: choice\n")
 	sb.WriteString("        options:\n")
-	for _, env := range g.config.Environments {
+	promoted := g.config.Environments
+	if len(promoted) > 0 {
+		promoted = promoted[1:]
+	}
+	for _, env := range promoted {
 		fmt.Fprintf(sb, "          - %s\n", env)
 	}
 
diff --git a/internal/generate/rollback_test.go b/internal/generate/rollback_test.go
index 659137e5..f7c02842 100644
--- a/internal/generate/rollback_test.go
+++ b/internal/generate/rollback_test.go
@@ -27,9 +27,19 @@ func rollbackTestConfig() *config.TrunkConfig {
 	}
 }
 
-func TestRollbackGenerator_Enabled_TrueWithOneEnv(t *testing.T) {
+func TestRollbackGenerator_Enabled_FalseWithOneEnv(t *testing.T) {
+	// A single-environment project's only env is the first (trunk-tracking)
+	// environment, which reverts via a merge to trunk, not a rollback. With no
+	// promoted environment to roll back, the workflow is not emitted, mirroring
+	// the hotfix generator.
 	cfg := &config.TrunkConfig{Environments: []string{"prod"}}
 	g := NewRollbackGenerator(cfg, "")
+	assert.False(t, g.Enabled())
+}
+
+func TestRollbackGenerator_Enabled_TrueWithTwoEnvs(t *testing.T) {
+	cfg := &config.TrunkConfig{Environments: []string{"dev", "prod"}}
+	g := NewRollbackGenerator(cfg, "")
 	assert.True(t, g.Enabled())
 }
 
@@ -39,6 +49,25 @@ func TestRollbackGenerator_Enabled_FalseWithZeroEnv(t *testing.T) {
 	assert.False(t, g.Enabled())
 }
 
+func TestRollbackGenerator_EnvironmentChoices_ExcludeFirstEnv(t *testing.T) {
+	cfg := &config.TrunkConfig{
+		TrunkBranch:  "main",
+		Environments: []string{"dev", "staging", "prod"},
+		Deploys: []config.DeployConfig{
+			{Name: "services", Workflow: ".github/workflows/deploy.yaml"},
+		},
+	}
+	content, err := NewRollbackGenerator(cfg, "").Generate()
+	assert.NoError(t, err)
+
+	// The first env tracks trunk and is refused by the runtime guard, so the
+	// dropdown must not offer it. The promoted envs remain selectable.
+	assert.NotContains(t, content, "          - dev\n",
+		"first environment must not be a rollback choice")
+	assert.Contains(t, content, "          - staging\n")
+	assert.Contains(t, content, "          - prod\n")
+}
+
 func TestRollbackGenerator_DispatchInputs(t *testing.T) {
 	g := NewRollbackGenerator(rollbackTestConfig(), "")
 	content, err := g.Generate()
diff --git a/internal/rollback/first_env_guard_test.go b/internal/rollback/first_env_guard_test.go
new file mode 100644
index 00000000..03935727
--- /dev/null
+++ b/internal/rollback/first_env_guard_test.go
@@ -0,0 +1,105 @@
+package rollback
+
+import (
+	"strings"
+	"testing"
+
+	"github.com/stablekernel/cascade/internal/config"
+)
+
+// The first environment tracks trunk and is never promoted into, so its
+// deploy-history ring is structurally always empty. A rollback there would
+// resolve a target from an empty or stale ring, which is a silent wrong target.
+// The guard makes that case fail fast with an actionable error. dev is the first
+// environment in the manifest writeManifest builds; prod is a promoted env.
+
+func TestPlan_FirstEnvironment_NoTarget_Guarded(t *testing.T) {
+	dir := t.TempDir()
+	path := writeManifest(t, dir, "prodsha9999999", "v1.9.0")
+	rb := newRollbacker(t, path, fakeHistory{})
+
+	_, err := rb.Plan("dev", "", "")
+	if err == nil {
+		t.Fatalf("expected guard error rolling back the first environment, got nil")
+	}
+	if !strings.Contains(err.Error(), "first environment") {
+		t.Errorf("error = %q, want it to name the first environment", err.Error())
+	}
+	if !strings.Contains(err.Error(), "dev") {
+		t.Errorf("error = %q, want it to name the env (dev)", err.Error())
+	}
+	if !strings.Contains(err.Error(), "trunk") {
+		t.Errorf("error = %q, want it to point at the trunk revert path", err.Error())
+	}
+}
+
+func TestPlan_FirstEnvironment_WithTarget_Guarded(t *testing.T) {
+	dir := t.TempDir()
+	path := writeManifest(t, dir, "prodsha9999999", "v1.9.0")
+	rb := newRollbacker(t, path, fakeHistory{})
+
+	// Even an explicit --to value that matches the first env's live state must be
+	// refused: the trunk-tracking env reverts via a merge, not a ring rollback.
+	_, err := rb.Plan("dev", "devsha1234567", "")
+	if err == nil {
+		t.Fatalf("expected guard error rolling back the first environment with --to, got nil")
+	}
+	if !strings.Contains(err.Error(), "first environment") {
+		t.Errorf("error = %q, want it to name the first environment", err.Error())
+	}
+}
+
+func TestPlan_FirstEnvironment_Deployable_Guarded(t *testing.T) {
+	dir := t.TempDir()
+	path := writeManifest(t, dir, "prodsha9999999", "v1.9.0")
+	rb := newRollbacker(t, path, fakeHistory{})
+
+	_, err := rb.Plan("dev", "", "services")
+	if err == nil {
+		t.Fatalf("expected guard error for a deployable-scoped first-env rollback, got nil")
+	}
+	if !strings.Contains(err.Error(), "first environment") {
+		t.Errorf("error = %q, want it to name the first environment", err.Error())
+	}
+}
+
+func TestPlan_PromotedEnvironment_NotGuarded(t *testing.T) {
+	dir := t.TempDir()
+	path := writeManifest(t, dir, "prodsha9999999", "v1.9.0")
+	rb := newRollbacker(t, path, fakeHistory{})
+
+	// prod is a promoted (non-first) env: the guard must not fire and the
+	// no-target default path must still resolve through the normal sources.
+	if _, err := rb.Plan("prod", "v1.9.0", ""); err != nil {
+		t.Fatalf("Plan on a promoted env should not be guarded: %v", err)
+	}
+}
+
+func TestApply_FirstEnvironment_Guarded(t *testing.T) {
+	dir := t.TempDir()
+	path := writeManifest(t, dir, "prodsha9999999", "v1.9.0")
+	rb := newRollbacker(t, path, fakeHistory{})
+
+	// A plan constructed directly for the first env (bypassing Plan) must still be
+	// refused by Apply: the guard is defense in depth on the only mutating path.
+	plan := &Plan{
+		Environment: "dev",
+		Target:      Target{SHA: "devsha1234567", Version: "v2.0.0-rc.1", Source: "state"},
+	}
+	err := rb.Apply(plan)
+	if err == nil {
+		t.Fatalf("expected Apply to refuse a first-environment rollback, got nil")
+	}
+	if !strings.Contains(err.Error(), "first environment") {
+		t.Errorf("error = %q, want it to name the first environment", err.Error())
+	}
+}
+
+// Guards must be inert when there is no parsed config to identify the first
+// environment, so a state-only manifest still resolves through the normal path.
+func TestFirstEnvErr_NoConfig_Inert(t *testing.T) {
+	rb := &Rollbacker{cicdFile: &config.CICDFile{}}
+	if err := rb.firstEnvErr("dev"); err != nil {
+		t.Errorf("firstEnvErr with no config should be nil, got %v", err)
+	}
+}
diff --git a/internal/rollback/rollback.go b/internal/rollback/rollback.go
index ebfc2d96..d0436360 100644
--- a/internal/rollback/rollback.go
+++ b/internal/rollback/rollback.go
@@ -173,6 +173,10 @@ func (r *Rollbacker) Plan(env, to, deployable string) (*Plan, error) {
 		return nil, fmt.Errorf("unknown environment %q (not declared in config.environments and has no recorded state)", env)
 	}
 
+	if err := r.firstEnvErr(env); err != nil {
+		return nil, err
+	}
+
 	current := r.cicdFile.State[env]
 	plan := &Plan{
 		Environment: env,
@@ -390,6 +394,9 @@ func (r *Rollbacker) Apply(plan *Plan) error {
 	if plan == nil {
 		return fmt.Errorf("nil plan")
 	}
+	if err := r.firstEnvErr(plan.Environment); err != nil {
+		return err
+	}
 	if plan.NoOp {
 		return nil
 	}
@@ -484,6 +491,24 @@ func (r *Rollbacker) writeConfig() error {
 	return nil
 }
 
+// firstEnvErr returns a guard error when env is the first (build target)
+// environment and nil otherwise. The first environment tracks trunk and is
+// never promoted into, so its deploy-history ring is structurally always empty:
+// a rollback there has no recorded prior target and would resolve a silent wrong
+// one from an empty or stale ring. The trunk-native undo for the first
+// environment is a revert merge to the trunk branch, not a rollback. The guard
+// is inert when no parsed config is available to identify the first environment,
+// so a state-only manifest still resolves through the normal path.
+func (r *Rollbacker) firstEnvErr(env string) error {
+	if r.cicdFile == nil || r.cicdFile.Config == nil {
+		return nil
+	}
+	if r.cicdFile.Config.IsFirstEnvironment(env) {
+		return fmt.Errorf("environment %q is the first environment; it tracks trunk and is never promoted into, so it has no rollback history. Revert it with a merge to the trunk branch instead of a rollback", env)
+	}
+	return nil
+}
+
 // knownEnvironment reports whether env is declared in config.environments or
 // has recorded state.
 func (r *Rollbacker) knownEnvironment(env string) bool {