diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 365b67a18..7ab80c751 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -29,6 +29,7 @@
 - Fixed `getSecretPlaceholderKey()`/`getExistingSecretPlaceholderKey()` defaulting their `keyDir` parameter to `getConfigRootDir()` (`~/.omp`) while `createAgentSession()` always passes the profile-scoped `agentDir` (`~/.omp/agent`, per `docs/secrets.md`) explicitly. A caller relying on the default read or minted a key file at a different path than live sessions use, so placeholders it created were never stable against SDK sessions. Both helpers now default to `getAgentDir()`.
 - Fixed a default (no custom `replacement`) `mode: "replace"` regex that cannot escape a 1–2 byte match (e.g. `.`, `[\s\S]`, `[\s\S]{2}`) still risking an unredacted round-trip: the previous key-derived same-length fallback marker was returned without checking it against the matched value, and since that marker is drawn from an alphabet the regex has already proven to match exhaustively, a real 1–2 byte secret that happened to equal it would ship to the provider unchanged. Such regex entries are now rejected outright — dropped with a warning when loaded from `secrets.yml`, dropped silently as a construction-time backstop otherwise — since no same-length marker can be guaranteed distinct from every possible match once the regex is proven to match every candidate in that alphabet.
 - Fixed a plain secret's `friendlyName` being accepted as a placeholder prefix when it was a lowercase or punctuated variant of the secret's own value (e.g. `friendlyName: "github_pat_abc123"` for a secret of the same content): the collision check compared the already-sanitized (uppercased, alphanumeric-only) friendly name against the secret's raw, case-sensitive value, so a case/punctuation variant slipped through and stamped most of the secret into every placeholder (`#GITHUBPATABC123_…#`). The secret value is now sanitized the same way before the comparison.
+- Fixed a regex-discovered secret's `friendlyName` collision check testing the already-sanitized (uppercased, separator-stripped) label against the configured regex instead of the label as written, so a case-sensitive or punctuated pattern (e.g. `tok_[a-z0-9]+`) missed a `friendlyName` that was itself a live match for that regex (e.g. `"tok_abc123"`), stamping the matched token — minus separators — into every placeholder (`#TOKABC123_…#`). The regex check now runs against the raw, pre-sanitization label, matching how the regex would actually encounter that text verbatim.
 
 ## [16.3.8] - 2026-07-05
 
diff --git a/packages/coding-agent/src/secrets/obfuscator.ts b/packages/coding-agent/src/secrets/obfuscator.ts
index 00453f153..123edc58f 100644
--- a/packages/coding-agent/src/secrets/obfuscator.ts
+++ b/packages/coding-agent/src/secrets/obfuscator.ts
@@ -1087,7 +1087,9 @@ export class SecretObfuscator {
 		// it; the secret still gets a bare (unprefixed) placeholder.
 		const requestedFriendlyName = friendlyName ? sanitizeSecretFriendlyName(friendlyName) : undefined;
 		const sanitizedFriendlyName =
-			requestedFriendlyName !== undefined && !this.#friendlyNameCollidesWithSecret(requestedFriendlyName)
+			requestedFriendlyName !== undefined &&
+			friendlyName !== undefined &&
+			!this.#friendlyNameCollidesWithSecret(requestedFriendlyName, friendlyName)
 				? requestedFriendlyName
 				: undefined;
 		const preferredBase = this.#resolvePreferredPlaceholderBase(baseKey);
@@ -1158,21 +1160,27 @@ export class SecretObfuscator {
 	// verbatim, model-visible prefix on every placeholder minted for THIS
 	// secret, baked in via an exact `#deobfuscateMap` entry rather than the
 	// alias fallback — so it needs its own check independent of the scan-skip
-	// alias guard in `#isGeneratedPlaceholder`. Reject when the label contains a
-	// sanitized (alnum-only, uppercased) form of a configured plain secret's
-	// value — the same normalization already applied to the label itself, so a
+	// alias guard in `#isGeneratedPlaceholder`. Reject when the SANITIZED label
+	// contains a sanitized (alnum-only, uppercased) form of a configured plain
+	// secret's value — comparing both sides through the same normalization so a
 	// lowercase or punctuated secret cannot smuggle itself through case or
-	// separator noise — or when any configured regex pattern matches the label
-	// — either means that text is meant to be redacted, not stamped unredacted
-	// onto every use of this secret.
-	#friendlyNameCollidesWithSecret(name: string): boolean {
+	// separator noise — or when any configured regex pattern matches the RAW
+	// (pre-sanitization) label. The regex check uses the raw label, not the
+	// sanitized one: a regex describes what a real secret occurrence looks like
+	// verbatim in text, so the question is whether this label's own literal
+	// characters are a value the regex would have redacted, not whether some
+	// unrelated case/punctuation-stripped rendering of it happens to match a
+	// pattern that never described that rendering. Either check means the text
+	// is meant to be redacted, not stamped unredacted onto every use of this
+	// secret.
+	#friendlyNameCollidesWithSecret(sanitizedName: string, rawName: string): boolean {
 		for (const secretValue of this.#configuredSecretValues) {
 			const sanitizedSecret = secretValue.replace(/[^A-Za-z0-9]/g, "").toUpperCase();
-			if (sanitizedSecret.length > 0 && name.includes(sanitizedSecret)) return true;
+			if (sanitizedSecret.length > 0 && sanitizedName.includes(sanitizedSecret)) return true;
 		}
 		for (const entry of this.#regexEntries) {
 			entry.regex.lastIndex = 0;
-			const matches = entry.regex.test(name);
+			const matches = entry.regex.test(rawName);
 			entry.regex.lastIndex = 0;
 			if (matches) return true;
 		}
diff --git a/packages/coding-agent/test/secrets-obfuscator.test.ts b/packages/coding-agent/test/secrets-obfuscator.test.ts
index b25ecf928..4b40c1de8 100644
--- a/packages/coding-agent/test/secrets-obfuscator.test.ts
+++ b/packages/coding-agent/test/secrets-obfuscator.test.ts
@@ -358,6 +358,30 @@ describe("SecretObfuscator friendlyName placeholders", () => {
 		expect(obfuscator.deobfuscate(obfuscated)).toBe(input);
 	});
 
+	it("rejects a regex entry friendlyName that is itself a live match for its own pattern", () => {
+		// `#friendlyNameCollidesWithSecret` used to run each regex entry's pattern
+		// against the SANITIZED friendly name (uppercased, non-alphanumeric
+		// stripped) instead of the raw one. A case-sensitive/punctuated pattern
+		// like `tok_[a-z0-9]+` requires a literal lowercase underscore, so it could
+		// never match the sanitized label "TOKABC123" even though the raw
+		// friendlyName "tok_abc123" is itself a live match for that very pattern.
+		// That let a secret-shaped friendlyName slip through and get stamped
+		// (minus separators, uppercased) into every placeholder minted for it. The
+		// check now runs the pattern against the raw, pre-sanitization
+		// friendlyName, so this case is caught and the secret falls back to a bare
+		// placeholder.
+		const secret = "tok_abc123";
+		const obfuscator = new SecretObfuscator([
+			{ type: "regex", content: "tok_[a-z0-9]+", friendlyName: "tok_abc123" },
+		]);
+		const input = `use ${secret} now`;
+		const obfuscated = obfuscator.obfuscate(input);
+
+		expect(obfuscated).not.toMatch(/TOKABC123_/);
+		expect(obfuscated).toMatch(/^use #[A-Z0-9]+:L# now$/);
+		expect(obfuscator.deobfuscate(obfuscated)).toBe(input);
+	});
+
 	it("does not replace plain secrets inside generated friendly placeholders", () => {
 		const longSecret = "long-secret-token";
 		const prefixSecret = "TOKENABC";