diff --git a/get-shit-done/workflows/execute-phase.md b/get-shit-done/workflows/execute-phase.md
index ad7ad361..e1416917 100644
--- a/get-shit-done/workflows/execute-phase.md
+++ b/get-shit-done/workflows/execute-phase.md
@@ -1315,13 +1315,32 @@ Read and follow `~/.claude/get-shit-done/workflows/transition.md`, passing throu
 
 **IMPORTANT: There is NO `/gsd-transition` command. Never suggest it. The transition workflow is internal only.**
 
+Check whether CONTEXT.md already exists for the next phase:
+
+```bash
+ls .planning/phases/*{next}*/{next}-CONTEXT.md 2>/dev/null || echo "no-context"
+```
+
+If CONTEXT.md does **not** exist for the next phase, present:
+
 ```
 ## ✓ Phase {X}: {Name} Complete
 
 /gsd-progress ${GSD_WS} — see updated roadmap
-/gsd-discuss-phase {next} ${GSD_WS} — discuss next phase before planning
-/gsd-plan-phase {next} ${GSD_WS} — plan next phase
-/gsd-execute-phase {next} ${GSD_WS} — execute next phase
+/gsd-discuss-phase {next} ${GSD_WS} — start here: discuss next phase before planning  ← recommended
+/gsd-plan-phase {next} ${GSD_WS} — plan next phase (skip discuss)
+/gsd-execute-phase {next} ${GSD_WS} — execute next phase (skip discuss and plan)
+```
+
+If CONTEXT.md **exists** for the next phase, present:
+
+```
+## ✓ Phase {X}: {Name} Complete
+
+/gsd-progress ${GSD_WS} — see updated roadmap
+/gsd-plan-phase {next} ${GSD_WS} — start here: plan next phase (CONTEXT.md already present)  ← recommended
+/gsd-discuss-phase {next} ${GSD_WS} — re-discuss next phase
+/gsd-execute-phase {next} ${GSD_WS} — execute next phase (skip planning)
 ```
 
 Only suggest the commands listed above. Do not invent or hallucinate command names.
diff --git a/tests/bug-2002-offer-next-context.test.cjs b/tests/bug-2002-offer-next-context.test.cjs
new file mode 100644
index 00000000..4144664c
--- /dev/null
+++ b/tests/bug-2002-offer-next-context.test.cjs
@@ -0,0 +1,86 @@
+/**
+ * Regression tests for bug #2002
+ *
+ * offer_next in execute-phase.md must present conditional next steps
+ * based on whether CONTEXT.md already exists for the next phase.
+ * The previous flat list offered all options equally with no primary
+ * recommendation, leaving agents without guidance on the correct first step.
+ *
+ * Fixed: offer_next now checks for {next}-CONTEXT.md in the phase directory.
+ * - If CONTEXT.md is missing: primary suggestion is /gsd-discuss-phase
+ * - If CONTEXT.md exists: primary suggestion is /gsd-plan-phase
+ */
+
+'use strict';
+
+const { describe, test } = require('node:test');
+const assert = require('node:assert/strict');
+const fs = require('node:fs');
+const path = require('node:path');
+
+const workflowPath = path.resolve(
+  __dirname, '..', 'get-shit-done', 'workflows', 'execute-phase.md'
+);
+
+describe('bug #2002: offer_next checks CONTEXT.md before suggesting next step', () => {
+  let content;
+
+  // Read once — all tests share the same file content
+  test('setup: workflow file is readable', () => {
+    content = fs.readFileSync(workflowPath, 'utf-8');
+    assert.ok(content.length > 0, 'execute-phase.md must not be empty');
+  });
+
+  test('offer_next section checks for CONTEXT.md existence', () => {
+    content = content || fs.readFileSync(workflowPath, 'utf-8');
+    // The workflow must check for CONTEXT.md in the next phase directory
+    assert.ok(
+      content.includes('CONTEXT.md'),
+      'offer_next must reference CONTEXT.md to determine primary next step'
+    );
+  });
+
+  test('offer_next presents /gsd-discuss-phase when CONTEXT.md does not exist', () => {
+    content = content || fs.readFileSync(workflowPath, 'utf-8');
+    // Must have a conditional path where discuss-phase is the primary step
+    // when CONTEXT.md is missing — look for proximity of "not exist"/"missing"/
+    // "does not exist" and "gsd-discuss-phase" in the offer_next step
+    const offerNextIdx = content.indexOf('offer_next');
+    assert.ok(offerNextIdx !== -1, 'offer_next step must exist');
+
+    // Use 5000-char window — the step is ~60 lines of prose before the conditionals
+    const offerNextSection = content.slice(offerNextIdx, offerNextIdx + 5000);
+    assert.ok(
+      /CONTEXT\.md.*does not exist|CONTEXT\.md.*not.*exist|If CONTEXT\.md does/i.test(offerNextSection) ||
+      /gsd-discuss-phase.*recommended|recommended.*gsd-discuss-phase/i.test(offerNextSection),
+      'offer_next must present /gsd-discuss-phase as primary when CONTEXT.md does not exist'
+    );
+  });
+
+  test('offer_next presents /gsd-plan-phase when CONTEXT.md exists', () => {
+    content = content || fs.readFileSync(workflowPath, 'utf-8');
+    const offerNextIdx = content.indexOf('offer_next');
+    assert.ok(offerNextIdx !== -1, 'offer_next step must exist');
+
+    const offerNextSection = content.slice(offerNextIdx, offerNextIdx + 5000);
+    assert.ok(
+      /CONTEXT\.md.*exists|exists.*CONTEXT\.md|If CONTEXT\.md/i.test(offerNextSection),
+      'offer_next must present /gsd-plan-phase as primary when CONTEXT.md exists'
+    );
+  });
+
+  test('offer_next section contains at least one conditional guard before listing commands', () => {
+    content = content || fs.readFileSync(workflowPath, 'utf-8');
+    const offerNextIdx = content.indexOf('offer_next');
+    assert.ok(offerNextIdx !== -1, 'offer_next step must exist');
+
+    const offerNextSection = content.slice(offerNextIdx, offerNextIdx + 5000);
+
+    // The fixed version must contain at least one "If CONTEXT.md" conditional
+    // guard before presenting command options. The old flat list had no guard.
+    assert.ok(
+      /If CONTEXT\.md/i.test(offerNextSection),
+      'offer_next must contain at least one "If CONTEXT.md" conditional guard'
+    );
+  });
+});