diff --git a/src/tmpfiles/tmpfiles.c b/src/tmpfiles/tmpfiles.c
index 705721ffbd..020219b176 100644
--- a/src/tmpfiles/tmpfiles.c
+++ b/src/tmpfiles/tmpfiles.c
@@ -69,6 +69,7 @@
 #include "terminal-util.h"
 #include "umask-util.h"
 #include "user-util.h"
+#include "virt.h"
 
 /* This reads all files listed in /etc/tmpfiles.d/?*.conf and creates
  * them in the file system. This is intended to be used to create
@@ -225,17 +226,12 @@ static const char *const creation_mode_verb_table[_CREATION_MODE_MAX] = {
 
 DEFINE_PRIVATE_STRING_TABLE_LOOKUP_TO_STRING(creation_mode_verb, CreationMode);
 
-static int specifier_machine_id_safe(char specifier, const void *data, const char *root, const void *userdata, char **ret) {
-        int r;
-
-        /* If /etc/machine_id is missing or empty (e.g. in a chroot environment) return a recognizable error
-         * so that the caller can skip the rule gracefully. */
-
-        r = specifier_machine_id(specifier, data, root, userdata, ret);
-        if (IN_SET(r, -ENOENT, -ENOMEDIUM))
-                return -ENXIO;
-
-        return r;
+/* Different kinds of errors that mean that information is not available in the environment. */
+static inline bool ERRNO_IS_NOINFO(int r) {
+        return IN_SET(abs(r),
+                      EUNATCH,    /* os-release or machine-id missing */
+                      ENOMEDIUM,  /* machine-id or another file empty */
+                      ENXIO);     /* env var is unset */
 }
 
 static int specifier_directory(char specifier, const void *data, const char *root, const void *userdata, char **ret) {
@@ -290,20 +286,28 @@ static int specifier_directory(char specifier, const void *data, const char *roo
 static int log_unresolvable_specifier(const char *filename, unsigned line) {
         static bool notified = false;
 
-        /* In system mode, this is called when /etc is not fully initialized (e.g.
-         * in a chroot environment) where some specifiers are unresolvable. In user
-         * mode, this is called when some variables are not defined. These cases are
-         * not considered as an error so log at LOG_NOTICE only for the first time
-         * and then downgrade this to LOG_DEBUG for the rest. */
+        /* In system mode, this is called when /etc is not fully initialized and some specifiers are
+         * unresolvable. In user mode, this is called when some variables are not defined. These cases are
+         * not considered a fatal error, so log at LOG_NOTICE only for the first time and then downgrade this
+         * to LOG_DEBUG for the rest.
+         *
+         * If we're running in a chroot (--root was used or sd_booted() reports that systemd is not running),
+         * always use LOG_DEBUG. We may be called to initialize a chroot before booting and there is no
+         * expectation that machine-id and other files will be populated.
+         */
+
+        int log_level = notified || arg_root || running_in_chroot() > 0 ?
+                LOG_DEBUG : LOG_NOTICE;
 
         log_syntax(NULL,
-                   notified ? LOG_DEBUG : LOG_NOTICE,
+                   log_level,
                    filename, line, 0,
-                   "Failed to resolve specifier: %s, skipping",
+                   "Failed to resolve specifier: %s, skipping.",
                    arg_user ? "Required $XDG_... variable not defined" : "uninitialized /etc/ detected");
 
         if (!notified)
-                log_notice("All rules containing unresolvable specifiers will be skipped.");
+                log_full(log_level,
+                         "All rules containing unresolvable specifiers will be skipped.");
 
         notified = true;
         return 0;
@@ -320,15 +324,15 @@ static int user_config_paths(char*** ret) {
                 return r;
 
         r = xdg_user_config_dir(&persistent_config, "/user-tmpfiles.d");
-        if (r < 0 && r != -ENXIO)
+        if (r < 0 && !ERRNO_IS_NOINFO(r))
                 return r;
 
         r = xdg_user_runtime_dir(&runtime_config, "/user-tmpfiles.d");
-        if (r < 0 && r != -ENXIO)
+        if (r < 0 && !ERRNO_IS_NOINFO(r))
                 return r;
 
         r = xdg_user_data_dir(&data_home, "/user-tmpfiles.d");
-        if (r < 0 && r != -ENXIO)
+        if (r < 0 && !ERRNO_IS_NOINFO(r))
                 return r;
 
         r = strv_extend_strv_concat(&res, config_dirs, "/user-tmpfiles.d");
@@ -3151,7 +3155,7 @@ static int parse_line(
                 { 'B', specifier_os_build_id,     NULL },
                 { 'H', specifier_hostname,        NULL },
                 { 'l', specifier_short_hostname,  NULL },
-                { 'm', specifier_machine_id_safe, NULL },
+                { 'm', specifier_machine_id,      NULL },
                 { 'o', specifier_os_id,           NULL },
                 { 'v', specifier_kernel_release,  NULL },
                 { 'w', specifier_os_version_id,   NULL },
@@ -3231,7 +3235,7 @@ static int parse_line(
         i.try_replace = try_replace;
 
         r = specifier_printf(path, PATH_MAX-1, specifier_table, arg_root, NULL, &i.path);
-        if (r == -ENXIO)
+        if (ERRNO_IS_NOINFO(r))
                 return log_unresolvable_specifier(fname, line);
         if (r < 0) {
                 if (IN_SET(r, -EINVAL, -EBADSLT))
@@ -3419,7 +3423,7 @@ static int parse_line(
         if (!unbase64) {
                 /* Do specifier expansion except if base64 mode is enabled */
                 r = specifier_expansion_from_arg(specifier_table, &i);
-                if (r == -ENXIO)
+                if (ERRNO_IS_NOINFO(r))
                         return log_unresolvable_specifier(fname, line);
                 if (r < 0) {
                         if (IN_SET(r, -EINVAL, -EBADSLT))
@@ -3437,7 +3441,8 @@ static int parse_line(
                 r = read_credential(i.argument, &i.binary_argument, &i.binary_argument_size);
                 if (IN_SET(r, -ENXIO, -ENOENT)) {
                         /* Silently skip over lines that have no credentials passed */
-                        log_syntax(NULL, LOG_INFO, fname, line, 0, "Credential '%s' not specified, skipping line.", i.argument);
+                        log_syntax(NULL, LOG_INFO, fname, line, 0,
+                                   "Credential '%s' not specified, skipping line.", i.argument);
                         return 0;
                 }
                 if (r < 0)