Thanks for the detailed diagnosis, Bruno. To try to fix the problems I installed the attached patches into Gnulib. If I understand things correctly, these patches should fix the 0.1% failure rate you observed on 64-bit mingw. They also fix a minor security leak I discovered: in rare cases, ASLR entropy was used to generate publicly visible file names, which is a no-no as that might help an attacker infer the randomized layout of a victim process.

These fixes follow some but not all the suggestions you made. The basic problem I saw was that tempname.c was using too much belt-and-suspenders code, so much so that the combination of belts and suspenders misbehaved. I simplified it a bit and this removed the need for some of the suggestions.

These fixes should be merged into glibc upstream since they fix glibc bugs; I plan to follow up on that shortly.
From 8304617684ba7f71c36fcf49786d3b279dfbefc3 Mon Sep 17 00:00:00 2001
From: Paul Eggert <egg...@cs.ucla.edu>
Date: Mon, 22 Aug 2022 12:22:52 -0700
Subject: [PATCH 1/3] tempname: merge 64-bit time_t fix from glibc

This merges glibc commit 52a5fe70a2c77935afe807fb6e904e512ddd894e
"Use 64 bit time_t stat internally".
* lib/tempname.c (struct_stat64) [_LIBC]: Use struct __stat64_t64.
(__lstat64_time64) [!_LIBC]: Rename from __lstat64.
All uses changed.
(direxists): Use __stat64_time64 instead of __stat64.
---
 ChangeLog      | 10 ++++++++++
 lib/tempname.c |  8 ++++----
 2 files changed, 14 insertions(+), 4 deletions(-)

diff --git a/ChangeLog b/ChangeLog
index de113ce081..adb445ddcf 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,3 +1,13 @@
+2022-08-22  Paul Eggert  <egg...@cs.ucla.edu>
+
+	tempname: merge 64-bit time_t fix from glibc
+	This merges glibc commit 52a5fe70a2c77935afe807fb6e904e512ddd894e
+	"Use 64 bit time_t stat internally".
+	* lib/tempname.c (struct_stat64) [_LIBC]: Use struct __stat64_t64.
+	(__lstat64_time64) [!_LIBC]: Rename from __lstat64.
+	All uses changed.
+	(direxists): Use __stat64_time64 instead of __stat64.
+
 2022-08-16  Bruno Haible  <br...@clisp.org>
 
 	tempname: Add more tests.
diff --git a/lib/tempname.c b/lib/tempname.c
index 5adfe629a8..4f615b90b9 100644
--- a/lib/tempname.c
+++ b/lib/tempname.c
@@ -55,14 +55,14 @@
 #include <time.h>
 
 #if _LIBC
-# define struct_stat64 struct stat64
+# define struct_stat64 struct __stat64_t64
 # define __secure_getenv __libc_secure_getenv
 #else
 # define struct_stat64 struct stat
 # define __gen_tempname gen_tempname
 # define __mkdir mkdir
 # define __open open
-# define __lstat64(file, buf) lstat (file, buf)
+# define __lstat64_time64(file, buf) lstat (file, buf)
 # define __stat64(file, buf) stat (file, buf)
 # define __getrandom getrandom
 # define __clock_gettime64 clock_gettime
@@ -105,7 +105,7 @@ static int
 direxists (const char *dir)
 {
   struct_stat64 buf;
-  return __stat64 (dir, &buf) == 0 && S_ISDIR (buf.st_mode);
+  return __stat64_time64 (dir, &buf) == 0 && S_ISDIR (buf.st_mode);
 }
 
 /* Path search algorithm, for tmpnam, tmpfile, etc.  If DIR is
@@ -197,7 +197,7 @@ try_nocreate (char *tmpl, _GL_UNUSED void *flags)
 {
   struct_stat64 st;
 
-  if (__lstat64 (tmpl, &st) == 0 || errno == EOVERFLOW)
+  if (__lstat64_time64 (tmpl, &st) == 0 || errno == EOVERFLOW)
     __set_errno (EEXIST);
   return errno == ENOENT ? 0 : -1;
 }
-- 
2.37.2

From 9ce573cde017182a69881241e8565ec04e5bc728 Mon Sep 17 00:00:00 2001
From: Paul Eggert <egg...@cs.ucla.edu>
Date: Mon, 22 Aug 2022 12:07:27 -0700
Subject: [PATCH 2/3] tempname: fix multithreading, ASLR leak etc.

Fix problems with tempname and multithreading, entropy loss,
and missing clock data (this last on non-GNU platforms).
See analysis by Bruno Haible in:
https://bugs.gnu.org/57129#149
While looking into this, I noticed that tempname can leak
info derived from ASLR into publicly-visible file names,
which is a no-no.  Fix that too.
* lib/tempname.c: Don't include stdalign.h.
(HAS_CLOCK_ENTROPY): Remove.
(mix_random_values): New function.
(random_bits): Use it.  Args are now new value address and
old value, and this function now returns a success indicator.
Omit old USE_GETRANDOM argument: always try getrandom now, as
there is no good reason not to now that GRND_NONBLOCK is used.
Caller changed.  Use CLOCK_REALTIME for for ersatz entropy,
as CLOCK_MONOTONIC doesn't work on some platforms.
Also, mix in ersatz entropy from tv_sec and from clock ().
(try_tempname_len): Do not mix in ASLR-based entropy, as
the result is published to the world and ASLR should be private.
Do not try to use a static var as that has issues if multithreaded.
Instead, simply generate new random bits.
Worry about bias only with high-quality random bits.
* modules/tempname (Depends-on): Do not depend on stdalign.
---
 ChangeLog        | 25 +++++++++++++
 lib/tempname.c   | 97 +++++++++++++++++++++++++-----------------------
 modules/tempname |  1 -
 3 files changed, 76 insertions(+), 47 deletions(-)

diff --git a/ChangeLog b/ChangeLog
index adb445ddcf..ed99c845f7 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,5 +1,30 @@
 2022-08-22  Paul Eggert  <egg...@cs.ucla.edu>
 
+	tempname: fix multithreading, ASLR leak etc.
+	Fix problems with tempname and multithreading, entropy loss,
+	and missing clock data (this last on non-GNU platforms).
+	See analysis by Bruno Haible in:
+	https://bugs.gnu.org/57129#149
+	While looking into this, I noticed that tempname can leak
+	info derived from ASLR into publicly-visible file names,
+	which is a no-no.  Fix that too.
+	* lib/tempname.c: Don't include stdalign.h.
+	(HAS_CLOCK_ENTROPY): Remove.
+	(mix_random_values): New function.
+	(random_bits): Use it.  Args are now new value address and
+	old value, and this function now returns a success indicator.
+	Omit old USE_GETRANDOM argument: always try getrandom now, as
+	there is no good reason not to now that GRND_NONBLOCK is used.
+	Caller changed.  Use CLOCK_REALTIME for for ersatz entropy,
+	as CLOCK_MONOTONIC doesn't work on some platforms.
+	Also, mix in ersatz entropy from tv_sec and from clock ().
+	(try_tempname_len): Do not mix in ASLR-based entropy, as
+	the result is published to the world and ASLR should be private.
+	Do not try to use a static var as that has issues if multithreaded.
+	Instead, simply generate new random bits.
+	Worry about bias only with high-quality random bits.
+	* modules/tempname (Depends-on): Do not depend on stdalign.
+
 	tempname: merge 64-bit time_t fix from glibc
 	This merges glibc commit 52a5fe70a2c77935afe807fb6e904e512ddd894e
 	"Use 64 bit time_t stat internally".
diff --git a/lib/tempname.c b/lib/tempname.c
index 4f615b90b9..bc1f7c14dd 100644
--- a/lib/tempname.c
+++ b/lib/tempname.c
@@ -48,7 +48,6 @@
 #include <string.h>
 
 #include <fcntl.h>
-#include <stdalign.h>
 #include <stdint.h>
 #include <sys/random.h>
 #include <sys/stat.h>
@@ -77,26 +76,55 @@ typedef uint_fast64_t random_value;
 #define BASE_62_DIGITS 10 /* 62**10 < UINT_FAST64_MAX */
 #define BASE_62_POWER (62LL * 62 * 62 * 62 * 62 * 62 * 62 * 62 * 62 * 62)
 
-#if _LIBC || (defined CLOCK_MONOTONIC && HAVE_CLOCK_GETTIME)
-# define HAS_CLOCK_ENTROPY true
-#else
-# define HAS_CLOCK_ENTROPY false
-#endif
+/* Return the result of mixing the entropy from R and S.
+   Assume that R and S are not particularly random,
+   and that the result should look randomish to an untrained eye.  */
 
 static random_value
-random_bits (random_value var, bool use_getrandom)
+mix_random_values (random_value r, random_value s)
+{
+  /* As this code is used only when high-quality randomness is neither
+     available nor necessary, there is no need for fancier polynomials
+     such as those in the Linux kernel's 'random' driver.  */
+  return (2862933555777941757 * r + 3037000493) ^ s;
+}
+
+/* Set *R to a random value.
+   Return true if *R is set to high-quality value taken from getrandom.
+   Otherwise return false, falling back to a low-quality *R that might
+   depend on S.
+
+   This function returns false only when getrandom fails.
+   On GNU systems this should happen only early in the boot process,
+   when the fallback should be good enough for programs using tempname
+   because any attacker likely has root privileges already.  */
+
+static bool
+random_bits (random_value *r, random_value s)
 {
-  random_value r;
   /* Without GRND_NONBLOCK it can be blocked for minutes on some systems.  */
-  if (use_getrandom && __getrandom (&r, sizeof r, GRND_NONBLOCK) == sizeof r)
-    return r;
-#if HAS_CLOCK_ENTROPY
-  /* Add entropy if getrandom did not work.  */
+  if (__getrandom (r, sizeof *r, GRND_NONBLOCK) == sizeof *r)
+    return true;
+
+  /* If getrandom did not work, use ersatz entropy based on low-order
+     clock bits.  On GNU systems getrandom should fail only
+     early in booting, when ersatz should be good enough.
+     Do not use ASLR-based entropy, as that would leak ASLR info into
+     the resulting file name which is typically public.
+
+     Of course we are in a state of sin here.  */
+
+  random_value v = 0;
+
+#if _LIBC || (defined CLOCK_REALTIME && HAVE_CLOCK_GETTIME)
   struct __timespec64 tv;
-  __clock_gettime64 (CLOCK_MONOTONIC, &tv);
-  var ^= tv.tv_nsec;
+  __clock_gettime64 (CLOCK_REALTIME, &tv);
+  v = mix_random_values (v, tv.tv_sec);
+  v = mix_random_values (v, tv.tv_nsec);
 #endif
-  return 2862933555777941757 * var + 3037000493;
+
+  *r = mix_random_values (v, clock ());
+  return false;
 }
 
 #if _LIBC
@@ -267,32 +295,15 @@ try_tempname_len (char *tmpl, int suffixlen, void *args,
   unsigned int attempts = ATTEMPTS_MIN;
 #endif
 
-  /* A random variable.  The initial value is used only the for fallback path
-     on 'random_bits' on 'getrandom' failure.  Its initial value tries to use
-     some entropy from the ASLR and ignore possible bits from the stack
-     alignment.  */
-  random_value v = ((uintptr_t) &v) / alignof (max_align_t);
-
-#if !HAS_CLOCK_ENTROPY
-  /* Arrange gen_tempname to return less predictable file names on
-     systems lacking clock entropy <https://bugs.gnu.org/57129>.  */
-  static random_value prev_v;
-  v ^= prev_v;
-#endif
+  /* A random variable.  */
+  random_value v = 0;
 
   /* How many random base-62 digits can currently be extracted from V.  */
   int vdigits = 0;
 
-  /* Whether to consume entropy when acquiring random bits.  On the
-     first try it's worth the entropy cost with __GT_NOCREATE, which
-     is inherently insecure and can use the entropy to make it a bit
-     more secure.  On the (rare) second and later attempts it might
-     help against DoS attacks.  */
-  bool use_getrandom = tryfunc == try_nocreate;
-
-  /* Least unfair value for V.  If V is less than this, V can generate
-     BASE_62_DIGITS digits fairly.  Otherwise it might be biased.  */
-  random_value const unfair_min
+  /* Least biased value for V.  If V is less than this, V can generate
+     BASE_62_DIGITS unbiased digits.  Otherwise the digits are biased.  */
+  random_value const biased_min
     = RANDOM_VALUE_MAX - RANDOM_VALUE_MAX % BASE_62_POWER;
 
   len = strlen (tmpl);
@@ -312,12 +323,9 @@ try_tempname_len (char *tmpl, int suffixlen, void *args,
         {
           if (vdigits == 0)
             {
-              do
-                {
-                  v = random_bits (v, use_getrandom);
-                  use_getrandom = true;
-                }
-              while (unfair_min <= v);
+              /* Worry about bias only if the bits are high quality.  */
+              while (random_bits (&v, v) && biased_min <= v)
+                continue;
 
               vdigits = BASE_62_DIGITS;
             }
@@ -331,9 +339,6 @@ try_tempname_len (char *tmpl, int suffixlen, void *args,
       if (fd >= 0)
         {
           __set_errno (save_errno);
-#if !HAS_CLOCK_ENTROPY
-          prev_v = v;
-#endif
           return fd;
         }
       else if (errno != EEXIST)
diff --git a/modules/tempname b/modules/tempname
index 4779735d9d..f1fb78e8ff 100644
--- a/modules/tempname
+++ b/modules/tempname
@@ -16,7 +16,6 @@ getrandom
 libc-config
 lstat
 mkdir
-stdalign
 stdbool
 stdint
 sys_stat
-- 
2.37.2

From d27c820595175ed563b4d4ee5d0f421011891572 Mon Sep 17 00:00:00 2001
From: Paul Eggert <egg...@cs.ucla.edu>
Date: Mon, 22 Aug 2022 15:43:18 -0500
Subject: [PATCH 3/3] tempname: don't lose entropy in seed

* lib/tempname.c (random_bits): Don't lose entropy in S
in the rare case where where the template has more than 10 Xs.
From a suggestion by Bruno Haible in:
https://bugs.gnu.org/57129#149
---
 ChangeLog      |  7 +++++++
 lib/tempname.c | 11 +++++++----
 2 files changed, 14 insertions(+), 4 deletions(-)

diff --git a/ChangeLog b/ChangeLog
index ed99c845f7..4d1c92cd81 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,5 +1,11 @@
 2022-08-22  Paul Eggert  <egg...@cs.ucla.edu>
 
+	tempname: don't lose entropy in seed
+	* lib/tempname.c (random_bits): Don't lose entropy in S
+	in the rare case where where the template has more than 10 Xs.
+	From a suggestion by Bruno Haible in:
+	https://bugs.gnu.org/57129#149
+
 	tempname: fix multithreading, ASLR leak etc.
 	Fix problems with tempname and multithreading, entropy loss,
 	and missing clock data (this last on non-GNU platforms).
@@ -23,6 +29,7 @@
 	Do not try to use a static var as that has issues if multithreaded.
 	Instead, simply generate new random bits.
 	Worry about bias only with high-quality random bits.
+
 	* modules/tempname (Depends-on): Do not depend on stdalign.
 
 	tempname: merge 64-bit time_t fix from glibc
diff --git a/lib/tempname.c b/lib/tempname.c
index bc1f7c14dd..0e2f29f5de 100644
--- a/lib/tempname.c
+++ b/lib/tempname.c
@@ -114,7 +114,7 @@ random_bits (random_value *r, random_value s)
 
      Of course we are in a state of sin here.  */
 
-  random_value v = 0;
+  random_value v = s;
 
 #if _LIBC || (defined CLOCK_REALTIME && HAVE_CLOCK_GETTIME)
   struct __timespec64 tv;
@@ -298,7 +298,9 @@ try_tempname_len (char *tmpl, int suffixlen, void *args,
   /* A random variable.  */
   random_value v = 0;
 
-  /* How many random base-62 digits can currently be extracted from V.  */
+  /* A value derived from the random variable, and how many random
+     base-62 digits can currently be extracted from VDIGBUF.  */
+  random_value vdigbuf;
   int vdigits = 0;
 
   /* Least biased value for V.  If V is less than this, V can generate
@@ -327,11 +329,12 @@ try_tempname_len (char *tmpl, int suffixlen, void *args,
               while (random_bits (&v, v) && biased_min <= v)
                 continue;
 
+              vdigbuf = v;
               vdigits = BASE_62_DIGITS;
             }
 
-          XXXXXX[i] = letters[v % 62];
-          v /= 62;
+          XXXXXX[i] = letters[vdigbuf % 62];
+          vdigbuf /= 62;
           vdigits--;
         }
 
-- 
2.37.2

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