diff --git a/packages/core/src/services/readiness/criteria.ts b/packages/core/src/services/readiness/criteria.ts
index b202a01..682a41e 100644
--- a/packages/core/src/services/readiness/criteria.ts
+++ b/packages/core/src/services/readiness/criteria.ts
@@ -287,6 +287,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "high",
       effort: "low",
+      docUrl: "https://docs.github.com/en/copilot/customizing-copilot/adding-repository-custom-instructions-for-github-copilot",
       check: async (context) => {
         const rootFound = await hasCustomInstructions(context.repoPath);
         if (rootFound.length === 0) {
@@ -399,6 +400,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "high",
       effort: "low",
+      docUrl: "https://code.visualstudio.com/docs/copilot/chat/mcp-servers",
       check: async (context) => {
         const found = await hasMcpConfig(context.repoPath);
         return {
@@ -419,6 +421,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "medium",
       effort: "medium",
+      docUrl: "https://docs.github.com/en/copilot/customizing-copilot/copilot-extensibility-overview",
       check: async (context) => {
         const found = await hasCustomAgents(
           context.repoPath,
@@ -442,6 +445,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "medium",
       effort: "medium",
+      docUrl: "https://docs.github.com/en/copilot/customizing-copilot/copilot-extensibility-overview",
       check: async (context) => {
         const found = await hasCopilotSkills(
           context.repoPath,
@@ -463,6 +467,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "medium",
       effort: "low",
+      docUrl: "https://microsoft.github.io/apm",
       check: async (context) => {
         const found = await hasApmConfig(context.repoPath);
         return {
@@ -482,6 +487,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "medium",
       effort: "low",
+      docUrl: "https://microsoft.github.io/apm",
       check: async (context) => {
         const hasConfig = await hasApmConfig(context.repoPath);
         if (!hasConfig) {
@@ -505,6 +511,7 @@ export function buildCriteria(): ReadinessCriterion[] {
       scope: "repo",
       impact: "high",
       effort: "medium",
+      docUrl: "https://microsoft.github.io/apm",
       check: async (context) => {
         const hasConfig = await hasApmConfig(context.repoPath);
         if (!hasConfig) {
diff --git a/packages/core/src/services/readiness/index.ts b/packages/core/src/services/readiness/index.ts
index 9691397..0dfd0c2 100644
--- a/packages/core/src/services/readiness/index.ts
+++ b/packages/core/src/services/readiness/index.ts
@@ -118,7 +118,8 @@ export async function runReadinessReport(options: ReadinessOptions): Promise<Rea
         effort: criterion.effort,
         status: result.status,
         reason: result.reason,
-        evidence: result.evidence
+        evidence: result.evidence,
+        docUrl: criterion.docUrl
       });
       continue;
     }
@@ -136,7 +137,8 @@ export async function runReadinessReport(options: ReadinessOptions): Promise<Rea
         impact: criterion.impact,
         effort: criterion.effort,
         status: "skip",
-        reason: "Run with --per-area for area breakdown."
+        reason: "Run with --per-area for area breakdown.",
+        docUrl: criterion.docUrl
       });
       continue;
     }
@@ -158,7 +160,8 @@ export async function runReadinessReport(options: ReadinessOptions): Promise<Rea
         impact: criterion.impact,
         effort: criterion.effort,
         status: "skip",
-        reason: "No application packages detected."
+        reason: "No application packages detected.",
+        docUrl: criterion.docUrl
       });
       continue;
     }
@@ -181,6 +184,7 @@ export async function runReadinessReport(options: ReadinessOptions): Promise<Rea
       effort: criterion.effort,
       status,
       reason: status === "pass" ? undefined : `Only ${passed}/${total} apps pass this check.`,
+      docUrl: criterion.docUrl,
       passRate,
       appSummary: { passed, total },
       appFailures: failures
@@ -217,7 +221,8 @@ export async function runReadinessReport(options: ReadinessOptions): Promise<Rea
           effort: criterion.effort,
           status: result.status,
           reason: result.reason,
-          evidence: result.evidence
+          evidence: result.evidence,
+          docUrl: criterion.docUrl
         });
       }
 
diff --git a/packages/core/src/services/readiness/types.ts b/packages/core/src/services/readiness/types.ts
index aede145..738e604 100644
--- a/packages/core/src/services/readiness/types.ts
+++ b/packages/core/src/services/readiness/types.ts
@@ -46,6 +46,7 @@ export type ReadinessCriterionResult = {
   status: ReadinessStatus;
   reason?: string;
   evidence?: string[];
+  docUrl?: string;
   passRate?: number;
   appSummary?: { passed: number; total: number };
   appFailures?: string[];
@@ -134,6 +135,7 @@ export type ReadinessCriterion = {
   scope: ReadinessScope;
   impact: "high" | "medium" | "low";
   effort: "low" | "medium" | "high";
+  docUrl?: string;
   check: (context: ReadinessContext, app?: RepoApp, area?: Area) => Promise<CheckResult>;
 };
 
diff --git a/packages/core/src/services/visualReport.ts b/packages/core/src/services/visualReport.ts
index e7500cd..0f920ee 100644
--- a/packages/core/src/services/visualReport.ts
+++ b/packages/core/src/services/visualReport.ts
@@ -171,6 +171,8 @@ export function generateVisualReport(options: VisualReportOptions): string {
     .fix-item-title { font-weight: 600; font-size: 13px; color: var(--color-fg-default); }
     .fix-item-reason { font-size: 12px; color: var(--color-fg-muted); margin-top: 2px; }
     .fix-item-badges { display: flex; gap: 6px; margin-top: 4px; }
+    .doc-link { font-size: 12px; color: var(--color-accent-fg); text-decoration: none; }
+    .doc-link:hover { text-decoration: underline; }
     .fix-badge {
       font-size: 11px;
       padding: 1px 8px;
@@ -561,7 +563,7 @@ export function generateVisualReport(options: VisualReportOptions): string {
                           .map(
                             (c) => `
                           <div class="criterion-row">
-                            <span>${escapeHtml(c.title)}</span>
+                            <span>${escapeHtml(c.title)}${c.status === "fail" && c.docUrl ? ` <a class="doc-link" href="${escapeHtml(c.docUrl)}" target="_blank" rel="noopener noreferrer">docs</a>` : ""}</span>
                             <span class="criterion-status ${c.status}">${c.status === "pass" ? "Pass" : c.status === "fail" ? "Fail" : "Skip"}</span>
                           </div>
                         `
@@ -749,6 +751,8 @@ function buildFixFirstHtml(reports: Array<{ repo: string; report: ReadinessRepor
                 <span class="fix-badge effort-${c.effort}">${c.effort} effort</span>
                 ${multiRepo ? `<span class="fix-badge impact-low">${repos.length} repo${repos.length > 1 ? "s" : ""}</span>` : ""}
               </div>
+              ${c.docUrl ? `<a class="doc-link" href="${escapeHtml(c.docUrl)}" target="_blank" rel="noopener noreferrer">Learn more &rarr;</a>` : ""}
+              </div>
             </div>
           </div>
         `
@@ -855,6 +859,7 @@ type AiToolingCriterionSummary = {
   status: "pass" | "fail";
   evidence: string[];
   reason: string;
+  docUrl?: string;
 };
 
 type AiToolingData = {
@@ -885,7 +890,8 @@ function calculateAiToolingData(
           totalRepos: 1,
           status: c.status === "pass" ? "pass" : "fail",
           evidence: c.evidence ? [...c.evidence] : [],
-          reason: c.reason || ""
+          reason: c.reason || "",
+          docUrl: c.docUrl
         });
       }
     }
@@ -992,7 +998,7 @@ function buildAiToolingHeroHtml(
                     ? `${c.passCount}/${c.totalRepos} repos`
                     : "Detected"
                   : escapeHtml(c.reason)
-              }</div>
+              }${c.status !== "pass" && c.docUrl ? ` <a class="doc-link" href="${escapeHtml(c.docUrl)}" target="_blank" rel="noopener noreferrer">Learn more &rarr;</a>` : ""}</div>
             </div>
           </div>
         `
diff --git a/webapp/frontend/src/report.js b/webapp/frontend/src/report.js
index 0537737..84b8b55 100644
--- a/webapp/frontend/src/report.js
+++ b/webapp/frontend/src/report.js
@@ -174,6 +174,7 @@ function buildFixFirst(report) {
               ${c.impact ? `<span class="fix-badge impact-${safeClass(c.impact, ALLOWED_IMPACT)}">${esc(c.impact)} impact</span>` : ""}
               ${c.effort ? `<span class="fix-badge effort-${safeClass(c.effort, ALLOWED_EFFORT)}">${esc(c.effort)} effort</span>` : ""}
             </div>
+            ${c.docUrl && isSafeDocUrl(c.docUrl) ? `<a class="doc-link" href="${esc(c.docUrl)}" target="_blank" rel="noopener noreferrer">Learn more →</a>` : ""}
           </div>
         </div>
       `
@@ -226,7 +227,7 @@ function buildAiToolingHero(report) {
             <div class="ai-criterion-icon ${safeClass(c.status, ALLOWED_STATUS)}">${c.status === "pass" ? "✓" : "✗"}</div>
             <div class="ai-criterion-text">
               <div class="ai-criterion-title">${icon} ${esc(c.title)}</div>
-              <div class="ai-criterion-reason">${c.status === "pass" ? "Detected" : esc(c.reason || "")}</div>
+              <div class="ai-criterion-reason">${c.status === "pass" ? "Detected" : esc(c.reason || "")}${c.status !== "pass" && c.docUrl && isSafeDocUrl(c.docUrl) ? ` <a class="doc-link" href="${esc(c.docUrl)}" target="_blank" rel="noopener noreferrer">Learn more →</a>` : ""}</div>
             </div>
           </div>`;
         })
@@ -588,3 +589,12 @@ function isGitHubUrl(url) {
     return false;
   }
 }
+
+function isSafeDocUrl(url) {
+  try {
+    const parsed = new URL(url);
+    return parsed.protocol === "https:";
+  } catch {
+    return false;
+  }
+}