JeremyDev87 · JeremyDev87 · May 5, 2026 · May 5, 2026
@@ -273,7 +273,7 @@ pub fn run_env_check_with_options(
 
             for contract_record in &contract_records {
                 for entry in &contract_record.parsed.entries {
-                    if !looks_like_secret(&entry.value) {
+                    if !looks_like_secret(&entry.key, &entry.value) {
                         continue;
                     }
 

@@ -126,6 +126,75 @@ fn env_check_matches_js_findings_for_duplicates_invalid_sync_secret_override_and
     );
 }
 
+#[test]
+fn env_example_secret_warning_uses_key_aware_classifier() {
+    let fixture = TempDir::new().expect("temp dir should exist");
+
+    write(
+        fixture.path().join(".env.example"),
+        "\
+AUTH_TOKEN=github-token
+SUPABASE_SERVICE_KEY=service-role-key
+SUPABASE_SERVICE_ROLE_KEY=service-role-key
+GOOGLE_SERVICE_ACCOUNT_KEY=service-account-key
+PRIVATE_KEY=private-key-value
+SHARED=sk_live_1234567890abcdef
+NEXT_PUBLIC_OKTA_CLIENT_ID=0oa1234567890abcdefghijkl
+VALIDATION_ISSUE_REPO=JeremyDev87/maximus-audit-signal
+VALIDATION_ISSUE_DASHBOARD_URL=https://github.com/JeremyDev87/maximus/issues/107
+VALIDATION_LABELS=enhancement,test,key-aware-env
+WINDOW_START_DATE=2026-05-05
+ERROR_PERCENT=100
+SYNC_HOURS=24
+SERVICE_WORKER_CACHE_KEY=v1
+PLACEHOLDER_TOKEN=change-me
+",
+    );
+
+    let project = discover_project(fixture.path()).expect("project should discover");
+    let outcome = run_env_check(&project).expect("check should run");
+    let env_file = fixture.path().join(".env.example");
+
+    for key in [
+        "AUTH_TOKEN",
+        "SUPABASE_SERVICE_KEY",
+        "SUPABASE_SERVICE_ROLE_KEY",
+        "GOOGLE_SERVICE_ACCOUNT_KEY",
+        "PRIVATE_KEY",
+        "SHARED",
+    ] {
+        assert_has_finding(
+            &outcome.findings,
+            &format!("env-example-secret:{}:{key}", env_file.to_string_lossy()),
+            Severity::Warn,
+            &format!(".env.example appears to contain a real value for \"{key}\""),
+            "Contract files should describe the interface, not ship concrete secrets.",
+            "Replace the value with a blank or placeholder string before sharing the repo.",
+            Some(env_file.clone()),
+            false,
+            &[],
+        );
+    }
+
+    for key in [
+        "NEXT_PUBLIC_OKTA_CLIENT_ID",
+        "VALIDATION_ISSUE_REPO",
+        "VALIDATION_ISSUE_DASHBOARD_URL",
+        "VALIDATION_LABELS",
+        "WINDOW_START_DATE",
+        "ERROR_PERCENT",
+        "SYNC_HOURS",
+        "SERVICE_WORKER_CACHE_KEY",
+        "PLACEHOLDER_TOKEN",
+    ] {
+        let id = format!("env-example-secret:{}:{key}", env_file.to_string_lossy());
+        assert!(
+            !outcome.findings.iter().any(|finding| finding.id == id),
+            "{key} should not produce env-example-secret"
+        );
+    }
+}
+
 #[test]
 fn env_check_plans_example_creation_when_runtime_env_files_exist_without_contract() {
     let fixture = TempDir::new().expect("temp dir should exist");

@@ -189,7 +189,7 @@ pub fn is_concrete_env_file_name(name: &str) -> bool {
     is_env_file_name(name) && !is_template_env_file_name(name)
 }
 
-pub fn looks_like_secret(value: &str) -> bool {
+pub fn looks_like_secret(key: &str, value: &str) -> bool {
     if value.is_empty() {
         return false;
     }
@@ -198,10 +198,11 @@ pub fn looks_like_secret(value: &str) -> bool {
         return false;
     }
 
-    value.len() >= 16
-        && value
-            .chars()
-            .all(|character| character.is_ascii_alphanumeric() || "/_+=-".contains(character))
+    if has_high_confidence_secret_value(value) {
+        return true;
+    }
+
+    is_secret_like_env_key(key)
 }
 
 fn split_env_assignment(line: &str) -> Option<(&str, &str)> {
@@ -280,6 +281,89 @@ fn is_placeholder_value(value: &str) -> bool {
         .unwrap_or(false)
 }
 
+fn has_high_confidence_secret_value(value: &str) -> bool {
+    let lower = value.to_ascii_lowercase();
+
+    value.contains("-----BEGIN PRIVATE KEY-----")
+        || lower.starts_with("sk_live_")
+        || lower.starts_with("sk_test_")
+        || lower.starts_with("ghp_")
+        || lower.starts_with("github_pat_")
+        || lower.starts_with("xoxb-")
+        || lower.starts_with("xoxp-")
+        || lower.starts_with("xoxa-")
+        || (value.len() == 20
+            && value.starts_with("AKIA")
+            && value
+                .chars()
+                .all(|character| character.is_ascii_uppercase() || character.is_ascii_digit()))
+        || (value.len() >= 35
+            && value.starts_with("AIza")
+            && value
+                .chars()
+                .all(|character| character.is_ascii_alphanumeric() || "-_".contains(character)))
+}
+
+fn is_secret_like_env_key(key: &str) -> bool {
+    let segments = env_key_segments(key);
+    if segments.is_empty() {
+        return false;
+    }
+
+    if contains_adjacent_segments(&segments, "PRIVATE", "KEY")
+        || contains_service_key_segments(&segments)
+    {
+        return true;
+    }
+
+    if segments.iter().any(|segment| {
+        matches!(
+            segment.as_str(),
+            "TOKEN" | "SECRET" | "PASSWORD" | "PASSWD" | "PWD"
+        )
+    }) {
+        return true;
+    }
+
+    if contains_adjacent_segments(&segments, "API", "KEY")
+        || contains_adjacent_segments(&segments, "ACCESS", "KEY")
+    {
+        return !is_public_key_identifier(&segments);
+    }
+
+    false
+}
+
+fn env_key_segments(key: &str) -> Vec<String> {
+    key.split(|character: char| !character.is_ascii_alphanumeric())
+        .filter(|segment| !segment.is_empty())
+        .map(|segment| segment.to_ascii_uppercase())
+        .collect()
+}
+
+fn contains_adjacent_segments(segments: &[String], left: &str, right: &str) -> bool {
+    segments
+        .windows(2)
+        .any(|window| window[0] == left && window[1] == right)
+}
+
+fn contains_service_key_segments(segments: &[String]) -> bool {
+    segments
+        .windows(2)
+        .any(|window| window[0] == "SERVICE" && window[1] == "KEY")
+        || segments.windows(3).any(|window| {
+            window[0] == "SERVICE"
+                && matches!(window[1].as_str(), "ROLE" | "ACCOUNT")
+                && window[2] == "KEY"
+        })
+}
+
+fn is_public_key_identifier(segments: &[String]) -> bool {
+    contains_adjacent_segments(segments, "PUBLIC", "KEY")
+        || contains_adjacent_segments(segments, "ANON", "KEY")
+        || contains_adjacent_segments(segments, "CLIENT", "ID")
+}
+
 fn normalize_env_template_source_group(group: EnvTemplateSourceGroup) -> EnvTemplateSourceGroup {
     let mut unique_keys = group
         .keys

@@ -144,9 +144,65 @@ fn env_helpers_match_current_js_behavior() {
     assert!(is_concrete_env_file_name(".env.local"));
     assert!(!is_concrete_env_file_name(".env."));
     assert!(!is_concrete_env_file_name(".env.template"));
-    assert!(looks_like_secret("supersecretvalue12345"));
-    assert!(!looks_like_secret("localhost"));
-    assert!(!looks_like_secret("your-api-key"));
+    assert!(looks_like_secret("AUTH_TOKEN", "supersecretvalue12345"));
+    assert!(!looks_like_secret("AUTH_TOKEN", "localhost"));
+    assert!(!looks_like_secret("AUTH_TOKEN", "your-api-key"));
+}
+
+#[test]
+fn env_secret_helper_is_key_aware() {
+    for (key, value) in [
+        ("AUTH_TOKEN", "github-token"),
+        ("DATABASE_SECRET", "secret-value"),
+        ("SUPABASE_SERVICE_KEY", "service-role-key"),
+        ("SUPABASE_SERVICE_ROLE_KEY", "service-role-key"),
+        ("GOOGLE_SERVICE_ACCOUNT_KEY", "service-account-key"),
+        ("PRIVATE_KEY", "private-key-value"),
+        ("API_KEY", "api-key-value"),
+        ("SHARED", "sk_live_1234567890abcdef"),
+    ] {
+        assert!(
+            looks_like_secret(key, value),
+            "{key}={value} should be treated as a secret-like template value"
+        );
+    }
+
+    for (key, value) in [
+        ("NEXT_PUBLIC_OKTA_CLIENT_ID", "0oa1234567890abcdefghijkl"),
+        ("VALIDATION_ISSUE_REPO", "JeremyDev87/maximus-audit-signal"),
+        (
+            "VALIDATION_ISSUE_DASHBOARD_URL",
+            "https://github.com/JeremyDev87/maximus/issues/107",
+        ),
+        ("VALIDATION_LABELS", "enhancement,test,key-aware-env"),
+        ("WINDOW_START_DATE", "2026-05-05"),
+        ("ERROR_PERCENT", "100"),
+        ("SYNC_HOURS", "24"),
+        ("SUPABASE_ANON_KEY", "supabase-anon-public-key"),
+        ("PUBLIC_KEY", "public-key-identifier"),
+        ("SERVICE_WORKER_CACHE_KEY", "v1"),
+    ] {
+        assert!(
+            !looks_like_secret(key, value),
+            "{key}={value} should be treated as public/config template data"
+        );
+    }
+
+    for placeholder in [
+        "change-me",
+        "placeholder",
+        "your-api-key",
+        "example",
+        "true",
+        "false",
+        "0",
+        "1",
+    ] {
+        assert!(
+            !looks_like_secret("AUTH_TOKEN", placeholder),
+            "{placeholder} should remain a non-warning placeholder"
+        );
+    }
 }
 
 #[test]

@@ -181,7 +181,7 @@ export async function runEnvCheck(project) {
 
       for (const contractRecord of contractRecords) {
         for (const entry of contractRecord.parsed.entries) {
-          if (!looksLikeSecret(entry.value)) {
+          if (!looksLikeSecret(entry.key, entry.value)) {
             continue;
           }
 

@@ -85,7 +85,7 @@ export function isConcreteEnvFileName(name) {
   return /^\.env(?:\..+)?$/u.test(name) && !isTemplateEnvFileName(name);
 }
 
-export function looksLikeSecret(value) {
+export function looksLikeSecret(key, value) {
   if (!value) {
     return false;
   }
@@ -94,13 +94,71 @@ export function looksLikeSecret(value) {
     return false;
   }
 
-  if (/^[A-Za-z0-9/_+=-]{16,}$/u.test(value)) {
+  if (hasHighConfidenceSecretValue(value)) {
     return true;
   }
 
+  return isSecretLikeEnvKey(key);
+}
+
+function hasHighConfidenceSecretValue(value) {
+  return (
+    value.includes("-----BEGIN PRIVATE KEY-----") ||
+    /^(?:sk_live_|sk_test_|ghp_|github_pat_|xox[abp]-)/iu.test(value) ||
+    /^AKIA[A-Z0-9]{16}$/u.test(value) ||
+    /^AIza[A-Za-z0-9_-]{31,}$/u.test(value)
+  );
+}
+
+function isSecretLikeEnvKey(key) {
+  const segments = key
+    .split(/[^A-Za-z0-9]+/u)
+    .filter(Boolean)
+    .map((segment) => segment.toUpperCase());
+
+  if (segments.length === 0) {
+    return false;
+  }
+
+  if (containsAdjacentSegments(segments, "PRIVATE", "KEY") || containsServiceKeySegments(segments)) {
+    return true;
+  }
+
+  if (segments.some((segment) => ["TOKEN", "SECRET", "PASSWORD", "PASSWD", "PWD"].includes(segment))) {
+    return true;
+  }
+
+  if (containsAdjacentSegments(segments, "API", "KEY") || containsAdjacentSegments(segments, "ACCESS", "KEY")) {
+    return !isPublicKeyIdentifier(segments);
+  }
+
   return false;
 }
 
+function containsAdjacentSegments(segments, left, right) {
+  return segments.some((segment, index) => segment === left && segments[index + 1] === right);
+}
+
+function containsServiceKeySegments(segments) {
+  return segments.some((segment, index) => {
+    if (segment !== "SERVICE") {
+      return false;
+    }
+
+    const next = segments[index + 1];
+    const following = segments[index + 2];
+    return next === "KEY" || ((next === "ROLE" || next === "ACCOUNT") && following === "KEY");
+  });
+}
+
+function isPublicKeyIdentifier(segments) {
+  return (
+    containsAdjacentSegments(segments, "PUBLIC", "KEY") ||
+    containsAdjacentSegments(segments, "ANON", "KEY") ||
+    containsAdjacentSegments(segments, "CLIENT", "ID")
+  );
+}
+
 export function parseExactGitignorePatterns(text) {
   return text
     .split(/\r?\n/u)