diff --git a/get-shit-done/workflows/discuss-phase.md b/get-shit-done/workflows/discuss-phase.md
index 90a9f84ae..d77fdf93a 100644
--- a/get-shit-done/workflows/discuss-phase.md
+++ b/get-shit-done/workflows/discuss-phase.md
@@ -162,6 +162,30 @@ Exit workflow.
 - This is the middle ground: user controls the discuss decisions, then plan+execute run autonomously
 </step>
 
+<step name="check_blocking_antipatterns" priority="first">
+**MANDATORY — Check for blocking anti-patterns before any other work.**
+
+Look for a `.continue-here.md` in the current phase directory:
+
+```bash
+ls ${phase_dir}/.continue-here.md 2>/dev/null || true
+```
+
+If `.continue-here.md` exists, parse its "Critical Anti-Patterns" table for rows with `severity` = `blocking`.
+
+**If one or more `blocking` anti-patterns are found:**
+
+This step cannot be skipped. Before proceeding to `check_existing` or any other step, the agent must demonstrate understanding of each blocking anti-pattern by answering all three questions for each one:
+
+1. **What is this anti-pattern?** — Describe it in your own words, not by quoting the handoff.
+2. **How did it manifest?** — Explain the specific failure that caused it to be recorded.
+3. **What structural mechanism (not acknowledgment) prevents it?** — Name the concrete step, checklist item, or enforcement mechanism that stops recurrence.
+
+Write these answers inline before continuing. If a blocking anti-pattern cannot be answered from the context in `.continue-here.md`, stop and ask the user for clarification.
+
+**If no `.continue-here.md` exists, or no `blocking` rows are found:** Proceed directly to `check_existing`.
+</step>
+
 <step name="check_existing">
 Check if CONTEXT.md already exists using `has_context` from init.
 
diff --git a/get-shit-done/workflows/execute-phase.md b/get-shit-done/workflows/execute-phase.md
index 888a7ba30..e8b49b4bf 100644
--- a/get-shit-done/workflows/execute-phase.md
+++ b/get-shit-done/workflows/execute-phase.md
@@ -110,6 +110,30 @@ fi
 ```
 </step>
 
+<step name="check_blocking_antipatterns" priority="first">
+**MANDATORY — Check for blocking anti-patterns before any other work.**
+
+Look for a `.continue-here.md` in the current phase directory:
+
+```bash
+ls ${phase_dir}/.continue-here.md 2>/dev/null || true
+```
+
+If `.continue-here.md` exists, parse its "Critical Anti-Patterns" table for rows with `severity` = `blocking`.
+
+**If one or more `blocking` anti-patterns are found:**
+
+This step cannot be skipped. Before proceeding to `check_interactive_mode` or any other step, the agent must demonstrate understanding of each blocking anti-pattern by answering all three questions for each one:
+
+1. **What is this anti-pattern?** — Describe it in your own words, not by quoting the handoff.
+2. **How did it manifest?** — Explain the specific failure that caused it to be recorded.
+3. **What structural mechanism (not acknowledgment) prevents it?** — Name the concrete step, checklist item, or enforcement mechanism that stops recurrence.
+
+Write these answers inline before continuing. If a blocking anti-pattern cannot be answered from the context in `.continue-here.md`, stop and ask the user for clarification.
+
+**If no `.continue-here.md` exists, or no `blocking` rows are found:** Proceed directly to `check_interactive_mode`.
+</step>
+
 <step name="check_interactive_mode">
 **Parse `--interactive` flag from $ARGUMENTS.**
 
diff --git a/get-shit-done/workflows/pause-work.md b/get-shit-done/workflows/pause-work.md
index 2442d4008..f9e41e53d 100644
--- a/get-shit-done/workflows/pause-work.md
+++ b/get-shit-done/workflows/pause-work.md
@@ -44,6 +44,9 @@ If phase is detected, proceed with phase handoff path. Otherwise use the first m
 6. **Human actions pending**: Things that need manual intervention (MCP setup, API keys, approvals, manual testing)
 7. **Background processes**: Any running servers/watchers that were part of the workflow
 8. **Files modified**: What's changed but not committed
+9. **Blocking constraints**: Anti-patterns or methodological failures encountered during this session that a resuming agent MUST be aware of before proceeding. Only include items discovered through actual failure — not warnings or predictions. Assign each constraint a `severity`:
+   - `blocking` — The resuming agent MUST demonstrate understanding before proceeding. The discuss-phase and execute-phase workflows will enforce a mandatory understanding check.
+   - `advisory` — Important context but does not gate resumption.
 
 Ask user for clarifications if needed via conversational questions.
 
@@ -111,12 +114,35 @@ status: in_progress
 last_updated: [timestamp from current-timestamp]
 ---
 
+# BLOCKING CONSTRAINTS — Read Before Anything Else
+
+> These are not suggestions. Each constraint below was discovered through failure.
+> Acknowledge each one explicitly before proceeding.
+
+- [ ] CONSTRAINT: [name] — [what it is] — [structural mitigation required]
+
+**Do not proceed until all boxes are checked.**
+
+_If no constraints have been identified yet, remove this section._
+
+## Critical Anti-Patterns
+
+| Pattern | Description | Severity | Prevention Mechanism |
+|---------|-------------|----------|---------------------|
+| [pattern name] | [what it is and how it manifested] | blocking | [structural step that prevents recurrence — not acknowledgment] |
+| [pattern name] | [what it is and how it manifested] | advisory | [guidance for avoiding it] |
+
+**Severity values:** `blocking` — resuming agent must pass understanding check before proceeding. `advisory` — important context, does not gate resumption.
+
+_Remove rows that do not apply. The discuss-phase and execute-phase workflows parse this table and enforce a mandatory understanding check for any `blocking` rows._
+
 <current_state>
 [Where exactly are we? Immediate context]
 </current_state>
 
 <completed_work>
 
+Completed Tasks:
 - Task 1: [name] - Done
 - Task 2: [name] - Done
 - Task 3: [name] - In progress, [what's done]
diff --git a/tests/anti-pattern-enforcement.test.cjs b/tests/anti-pattern-enforcement.test.cjs
new file mode 100644
index 000000000..10e2ed4da
--- /dev/null
+++ b/tests/anti-pattern-enforcement.test.cjs
@@ -0,0 +1,176 @@
+'use strict';
+
+/**
+ * Anti-Pattern Enforcement Tests (#1491)
+ *
+ * Validates that the handoff/resume system structurally enforces critical
+ * anti-patterns via severity levels and mandatory understanding checks.
+ */
+
+const { test, describe } = require('node:test');
+const assert = require('node:assert');
+const fs = require('fs');
+const path = require('path');
+
+const PAUSE_WORK = path.join(__dirname, '..', 'get-shit-done', 'workflows', 'pause-work.md');
+const DISCUSS_PHASE = path.join(__dirname, '..', 'get-shit-done', 'workflows', 'discuss-phase.md');
+const EXECUTE_PHASE = path.join(__dirname, '..', 'get-shit-done', 'workflows', 'execute-phase.md');
+
+describe('pause-work.md — severity column in Critical Anti-Patterns template', () => {
+  test('template includes a Severity column header in the anti-patterns table', () => {
+    const content = fs.readFileSync(PAUSE_WORK, 'utf-8');
+    assert.ok(
+      content.includes('Severity') || content.includes('severity'),
+      'pause-work.md template must include a Severity column in the anti-patterns table'
+    );
+  });
+
+  test('template documents "blocking" as a valid severity value', () => {
+    const content = fs.readFileSync(PAUSE_WORK, 'utf-8');
+    assert.ok(
+      content.includes('blocking'),
+      'pause-work.md must document "blocking" as a valid severity value'
+    );
+  });
+
+  test('template documents "advisory" as a valid severity value', () => {
+    const content = fs.readFileSync(PAUSE_WORK, 'utf-8');
+    assert.ok(
+      content.includes('advisory'),
+      'pause-work.md must document "advisory" as a valid severity value'
+    );
+  });
+
+  test('template explains that blocking anti-patterns trigger understanding check at resume', () => {
+    const content = fs.readFileSync(PAUSE_WORK, 'utf-8');
+    const hasExplanation =
+      (content.includes('blocking') && content.includes('understanding check')) ||
+      (content.includes('blocking') && content.includes('resume')) ||
+      (content.includes('blocking') && content.includes('understanding'));
+    assert.ok(
+      hasExplanation,
+      'pause-work.md must explain that blocking anti-patterns trigger an understanding check at resume'
+    );
+  });
+});
+
+describe('discuss-phase.md — blocking anti-pattern understanding check', () => {
+  test('workflow checks for .continue-here.md with blocking anti-patterns', () => {
+    const content = fs.readFileSync(DISCUSS_PHASE, 'utf-8');
+    const hasCheck =
+      content.includes('.continue-here.md') &&
+      (content.includes('blocking') || content.includes('anti-pattern'));
+    assert.ok(
+      hasCheck,
+      'discuss-phase.md must check for .continue-here.md blocking anti-patterns before proceeding'
+    );
+  });
+
+  test('workflow includes mandatory understanding verification for blocking anti-patterns', () => {
+    const content = fs.readFileSync(DISCUSS_PHASE, 'utf-8');
+    const hasVerification =
+      content.includes('understanding') ||
+      content.includes('understanding check') ||
+      content.includes('demonstrate understanding');
+    assert.ok(
+      hasVerification,
+      'discuss-phase.md must include a mandatory understanding verification step for blocking anti-patterns'
+    );
+  });
+
+  test('workflow specifies the three understanding check questions', () => {
+    const content = fs.readFileSync(DISCUSS_PHASE, 'utf-8');
+    // The three questions required by the issue
+    const hasWhatIs =
+      content.includes('What is this anti-pattern') ||
+      content.includes('what is this anti-pattern') ||
+      content.includes('What is the anti-pattern');
+    const hasHowManifest =
+      content.includes('How did it manifest') ||
+      content.includes('how did it manifest') ||
+      content.includes('manifest');
+    const hasPreventMechanism =
+      content.includes('structural mechanism') ||
+      content.includes('prevention') ||
+      content.includes('Prevention');
+    assert.ok(
+      hasWhatIs && hasHowManifest && hasPreventMechanism,
+      'discuss-phase.md must include the three understanding check questions: ' +
+      '"What is this anti-pattern?", "How did it manifest?", "What structural mechanism prevents it?"'
+    );
+  });
+
+  test('understanding check cannot be skipped (must be mandatory)', () => {
+    const content = fs.readFileSync(DISCUSS_PHASE, 'utf-8');
+    const hasMandatory =
+      content.includes('cannot be skipped') ||
+      content.includes('must not be skipped') ||
+      content.includes('mandatory') ||
+      content.includes('MANDATORY') ||
+      content.includes('required before');
+    assert.ok(
+      hasMandatory,
+      'discuss-phase.md must indicate that the blocking anti-pattern understanding check cannot be skipped'
+    );
+  });
+});
+
+describe('execute-phase.md — blocking anti-pattern understanding check', () => {
+  test('workflow checks for .continue-here.md with blocking anti-patterns', () => {
+    const content = fs.readFileSync(EXECUTE_PHASE, 'utf-8');
+    const hasCheck =
+      content.includes('.continue-here.md') &&
+      (content.includes('blocking') || content.includes('anti-pattern'));
+    assert.ok(
+      hasCheck,
+      'execute-phase.md must check for .continue-here.md blocking anti-patterns before proceeding'
+    );
+  });
+
+  test('workflow includes mandatory understanding verification for blocking anti-patterns', () => {
+    const content = fs.readFileSync(EXECUTE_PHASE, 'utf-8');
+    const hasVerification =
+      content.includes('understanding') ||
+      content.includes('understanding check') ||
+      content.includes('demonstrate understanding');
+    assert.ok(
+      hasVerification,
+      'execute-phase.md must include a mandatory understanding verification step for blocking anti-patterns'
+    );
+  });
+
+  test('workflow specifies the three understanding check questions', () => {
+    const content = fs.readFileSync(EXECUTE_PHASE, 'utf-8');
+    const hasWhatIs =
+      content.includes('What is this anti-pattern') ||
+      content.includes('what is this anti-pattern') ||
+      content.includes('What is the anti-pattern');
+    const hasHowManifest =
+      content.includes('How did it manifest') ||
+      content.includes('how did it manifest') ||
+      content.includes('manifest');
+    const hasPreventMechanism =
+      content.includes('structural mechanism') ||
+      content.includes('prevention') ||
+      content.includes('Prevention');
+    assert.ok(
+      hasWhatIs && hasHowManifest && hasPreventMechanism,
+      'execute-phase.md must include the three understanding check questions: ' +
+      '"What is this anti-pattern?", "How did it manifest?", "What structural mechanism prevents it?"'
+    );
+  });
+
+  test('understanding check cannot be skipped (must be mandatory)', () => {
+    const content = fs.readFileSync(EXECUTE_PHASE, 'utf-8');
+    const hasMandatory =
+      content.includes('cannot be skipped') ||
+      content.includes('must not be skipped') ||
+      content.includes('mandatory') ||
+      content.includes('MANDATORY') ||
+      content.includes('required before');
+    assert.ok(
+      hasMandatory,
+      'execute-phase.md must indicate that the blocking anti-pattern understanding check cannot be skipped'
+    );
+  });
+});