diff --git a/src/shutdown/detach-loopback.c b/src/shutdown/detach-loopback.c
index 8778a9e0c4..25288af221 100644
--- a/src/shutdown/detach-loopback.c
+++ b/src/shutdown/detach-loopback.c
@@ -17,6 +17,7 @@
 #include "blockdev-util.h"
 #include "detach-loopback.h"
 #include "device-util.h"
+#include "errno-util.h"
 #include "fd-util.h"
 #include "shutdown.h"
 
@@ -106,8 +107,12 @@ static int delete_loopback(const char *device) {
 
         fd = open(device, O_RDONLY|O_CLOEXEC);
         if (fd < 0) {
-                log_debug_errno(errno, "Failed to open loopback device %s: %m", device);
-                return errno == ENOENT ? 0 : -errno;
+                if (ERRNO_IS_DEVICE_ABSENT(errno)) {
+                        log_debug_errno(errno, "Tried to open loopback device '%s', but device disappeared by now, ignoring: %m", device);
+                        return 0;
+                }
+
+                return log_debug_errno(errno, "Failed to open loopback device '%s': %m", device);
         }
 
         /* Loopback block devices don't sync in-flight blocks when we clear the fd, hence sync explicitly
diff --git a/src/shutdown/detach-md.c b/src/shutdown/detach-md.c
index b1aad976e5..8b88d9b870 100644
--- a/src/shutdown/detach-md.c
+++ b/src/shutdown/detach-md.c
@@ -131,12 +131,21 @@ static int delete_md(RaidDevice *m) {
         assert(m->path);
 
         fd = open(m->path, O_RDONLY|O_CLOEXEC|O_EXCL);
-        if (fd < 0)
-                return -errno;
+        if (fd < 0) {
+                if (ERRNO_IS_DEVICE_ABSENT(errno)) {
+                        log_debug_errno(errno, "Tried to open MD device '%s', but device disappeared by now, ignoring: %m", m->path);
+                        return 0;
+                }
+
+                return log_debug_errno(errno, "Failed to open MD device '%s': %m", m->path);
+        }
 
         (void) sync_with_progress(fd);
 
-        return RET_NERRNO(ioctl(fd, STOP_ARRAY, NULL));
+        if (ioctl(fd, STOP_ARRAY, NULL) < 0)
+                return log_debug_errno(errno, "Failed to issue STOP_ARRAY on MD device '%s': %m", m->path);
+
+        return 1;
 }
 
 static int md_points_list_detach(RaidDevice **head, bool *changed, bool last_try) {
@@ -164,8 +173,9 @@ static int md_points_list_detach(RaidDevice **head, bool *changed, bool last_try
                         n_failed++;
                         continue;
                 }
+                if (r > 0)
+                        *changed = true;
 
-                *changed = true;
                 raid_device_free(head, m);
         }
 
diff --git a/src/shutdown/detach-swap.c b/src/shutdown/detach-swap.c
index fd7dcdf943..eafdc4341e 100644
--- a/src/shutdown/detach-swap.c
+++ b/src/shutdown/detach-swap.c
@@ -7,6 +7,7 @@
 
 #include "alloc-util.h"
 #include "detach-swap.h"
+#include "errno-util.h"
 #include "libmount-util.h"
 
 static void swap_device_free(SwapDevice **head, SwapDevice *m) {
@@ -74,20 +75,23 @@ int swap_list_get(const char *swaps, SwapDevice **head) {
 }
 
 static int swap_points_list_off(SwapDevice **head, bool *changed) {
-        int n_failed = 0;
+        int n_failed = 0, r;
 
         assert(head);
         assert(changed);
 
         LIST_FOREACH(swap_device, m, *head) {
                 log_info("Deactivating swap %s.", m->path);
-                if (swapoff(m->path) < 0) {
-                        log_warning_errno(errno, "Could not deactivate swap %s: %m", m->path);
+                r = RET_NERRNO(swapoff(m->path));
+                if (ERRNO_IS_NEG_DEVICE_ABSENT(r))
+                        log_debug_errno(r, "Tried to deactivate swap '%s', but swap disappeared by now, ignoring: %m", m->path);
+                else if (r < 0) {
+                        log_warning_errno(r, "Could not deactivate swap %s: %m", m->path);
                         n_failed++;
                         continue;
-                }
+                } else
+                        *changed = true;
 
-                *changed = true;
                 swap_device_free(head, m);
         }