diff --git a/projects/app/src/data/skills.ts b/projects/app/src/data/skills.ts
index b219807bd2..20fc7c4840 100644
--- a/projects/app/src/data/skills.ts
+++ b/projects/app/src/data/skills.ts
@@ -22,6 +22,7 @@ import {
 } from "@pinyinly/lib/collections";
 import { invariant } from "@pinyinly/lib/invariant";
 import type { Duration } from "date-fns";
+import { add } from "date-fns/add";
 import { sub } from "date-fns/sub";
 import { subDays } from "date-fns/subDays";
 import type { DeepReadonly } from "ts-essentials";
@@ -602,7 +603,14 @@ export function skillReviewQueue({
     } else {
       const skillRating = latestSkillRatings.get(skill);
       if (skillRating?.rating === Rating.Again) {
-        learningOrderRetry.push([skill, skillRating.createdAt]);
+        const debounceEndTime = add(skillRating.createdAt, skillRetryDebounce);
+        if (debounceEndTime <= now) {
+          // Debounce period has passed, treat as retry
+          learningOrderRetry.push([skill, skillRating.createdAt]);
+        } else {
+          // Still in debounce period, treat as due at debounce end time
+          learningOrderDue.push([skill, debounceEndTime]);
+        }
       } else if (srsState.nextReviewAt > now) {
         // Check if it should be the new newDueAt.
         if (newDueAt == null || newDueAt > srsState.nextReviewAt) {
@@ -868,6 +876,13 @@ export function skillKindToShorthand(skillKind: SkillKind): string {
  */
 export const skillDueWindow: Duration = { hours: 24 };
 
+/**
+ * Minimum time to wait before retry items (incorrect answers) become available
+ * again. This prevents consecutively asking related questions that would make
+ * the answers too obvious.
+ */
+export const skillRetryDebounce: Duration = { minutes: 5 };
+
 export function isOverdue(srsState: SrsStateType, now: Date): boolean {
   return srsState.nextReviewAt < sub(now, skillDueWindow);
 }
diff --git a/projects/app/test/client/query.test.ts b/projects/app/test/client/query.test.ts
index 4cba7f9cac..a38f744633 100644
--- a/projects/app/test/client/query.test.ts
+++ b/projects/app/test/client/query.test.ts
@@ -263,6 +263,29 @@ describe(
         });
       }
     });
+
+    test(`retry items are debounced for 5 minutes before becoming available again`, async () => {
+      const targetSkills: Skill[] = [`he:八:eight`];
+      const history: SkillReviewOp[] = [
+        `❌ he:八:eight`, // Get it wrong initially
+        `💤 2m`, // Wait 2 minutes (less than 5 minute debounce)
+      ];
+
+      // Within debounce period, item should be in due queue, not retry queue
+      const queue1 = await simulateSkillReviews({ targetSkills, history });
+      expect(queue1.retryCount).toBe(0); // Not in retry queue yet
+      expect(queue1.dueCount).toBe(1); // In due queue instead
+      expect(queue1.items[0]).toBe(`he:八:eight`); // Still available, but as due item
+
+      // Wait past the debounce period
+      history.push(`💤 4m`); // Total wait is now 6 minutes
+
+      // After debounce period, item should be in retry queue
+      const queue2 = await simulateSkillReviews({ targetSkills, history });
+      expect(queue2.retryCount).toBe(1); // Now in retry queue
+      expect(queue2.dueCount).toBe(0); // No longer in due queue
+      expect(queue2.items[0]).toBe(`he:八:eight`); // Still prioritized at front
+    });
   },
 );
 
diff --git a/projects/app/test/data/skills.test.ts b/projects/app/test/data/skills.test.ts
index 914a7d0be3..7a5fb2860c 100644
--- a/projects/app/test/data/skills.test.ts
+++ b/projects/app/test/data/skills.test.ts
@@ -509,7 +509,7 @@ describe(
                   [`he:丿:slash`, mockSrsState(时`-1d`, 时`-3m`)],
                 ]),
                 latestSkillRatings: new Map([
-                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-1m` }],
+                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-6m` }], // Past debounce period
                 ]),
                 isStructuralHanziWord,
               }),
@@ -571,8 +571,8 @@ describe(
                   [`he:丿:slash`, mockSrsState(时`-1d`, 时`-5m`)],
                 ]),
                 latestSkillRatings: new Map([
-                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-1m` }],
-                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-2m` }],
+                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-6m` }],
+                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-7m` }],
                 ]),
                 isStructuralHanziWord,
               }),
@@ -594,8 +594,8 @@ describe(
                   [`he:丿:slash`, mockSrsState(时`-1d`, 时`-5m`)],
                 ]),
                 latestSkillRatings: new Map([
-                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-2m` }],
-                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-1m` }],
+                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-7m` }],
+                  [`he:丿:slash`, { rating: Rating.Again, createdAt: 时`-6m` }],
                 ]),
                 isStructuralHanziWord,
               }),
@@ -609,6 +609,51 @@ describe(
             });
           },
         );
+
+        skillTest(
+          `failed skills are debounced for 5 minutes before becoming retry items`,
+          async ({ isStructuralHanziWord }) => {
+            const graph = await skillLearningGraph({
+              targetSkills: [`he:八:eight`],
+            });
+
+            // Test case 1: Within debounce period (skill failed 2 minutes ago)
+            expect(
+              skillReviewQueue({
+                graph,
+                skillSrsStates: new Map([
+                  [`he:八:eight`, mockSrsState(时`-1d`, 时`-10m`)],
+                ]),
+                latestSkillRatings: new Map([
+                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-2m` }],
+                ]),
+                isStructuralHanziWord,
+              }),
+            ).toMatchObject({
+              retryCount: 0, // Not yet available for retry
+              dueCount: 1, // In due queue instead
+              items: [`he:八:eight`], // Still available, but as due item
+            });
+
+            // Test case 2: After debounce period (skill failed 6 minutes ago)
+            expect(
+              skillReviewQueue({
+                graph,
+                skillSrsStates: new Map([
+                  [`he:八:eight`, mockSrsState(时`-1d`, 时`-10m`)],
+                ]),
+                latestSkillRatings: new Map([
+                  [`he:八:eight`, { rating: Rating.Again, createdAt: 时`-6m` }],
+                ]),
+                isStructuralHanziWord,
+              }),
+            ).toMatchObject({
+              retryCount: 1, // Now available for retry
+              dueCount: 0, // No longer in due queue
+              items: [`he:八:eight`], // Still prioritized at front
+            });
+          },
+        );
       });
 
       test(`prioritises due skills with highest value (rather than most over-due)`, async () => {