diff --git a/src/bootman/sysconfig.c b/src/bootman/sysconfig.c
index 7f3d6a6..ecb0f3b 100644
--- a/src/bootman/sysconfig.c
+++ b/src/bootman/sysconfig.c
@@ -77,9 +77,10 @@ SystemConfig *cbm_inspect_root(const char *path, bool image_mode)
          * UEFI. This is due to GPT being able to contain a legacy boot device
          * *and* an ESP at the same time. Native UEFI takes precedence.
          */
-        if (!native_uefi) {
+        if (!native_uefi || image_mode) {
                 boot = get_legacy_boot_device(realp);
         }
+
         if (boot) {
                 c->boot_device = boot;
                 c->wanted_boot_mask = BOOTLOADER_CAP_LEGACY | BOOTLOADER_CAP_GPT;
@@ -88,7 +89,9 @@ SystemConfig *cbm_inspect_root(const char *path, bool image_mode)
         }
 
         /* Now try to find the system ESP */
-        boot = get_boot_device();
+        if (!image_mode) {
+                boot = get_boot_device();
+        }
         if (boot) {
                 c->boot_device = boot;
                 c->wanted_boot_mask = BOOTLOADER_CAP_UEFI | BOOTLOADER_CAP_GPT;
diff --git a/src/bootman/update.c b/src/bootman/update.c
index 0a28326..0fb0ff3 100644
--- a/src/bootman/update.c
+++ b/src/bootman/update.c
@@ -184,6 +184,14 @@ static bool boot_manager_update_image(BootManager *self)
                 return false;
         }
 
+        /* Reinit bootloader for image mode to ensure the bootloader is then
+         * re-initialised for the current settings and environment.
+         */
+        if (!boot_manager_set_boot_dir(self, boot_dir)) {
+                LOG_FATAL("Cannot re-initialise bootloader for image mode");
+                return false;
+        }
+
         /* Sort them to find the newest kernel */
         nc_array_qsort(kernels, kernel_compare_reverse);
 
diff --git a/src/cli/ops/update.c b/src/cli/ops/update.c
index 2061b2c..edc4fe2 100644
--- a/src/cli/ops/update.c
+++ b/src/cli/ops/update.c
@@ -24,7 +24,6 @@ bool cbm_command_update(int argc, char **argv)
 {
         autofree(char) *root = NULL;
         autofree(BootManager) *manager = NULL;
-        bool image_mode = false;
         bool forced_image = false;
 
         if (!cli_default_args_init(&argc, &argv, &root, &forced_image)) {
@@ -47,7 +46,9 @@ bool cbm_command_update(int argc, char **argv)
                 }
                 /* Anything not / is image mode */
                 if (!streq(realp, "/")) {
-                        image_mode = true;
+                        boot_manager_set_image_mode(manager, true);
+                } else {
+                        boot_manager_set_image_mode(manager, forced_image);
                 }
 
                 /* CBM will check this again, we just needed to check for
@@ -56,19 +57,13 @@ bool cbm_command_update(int argc, char **argv)
                         return false;
                 }
         } else {
+                boot_manager_set_image_mode(manager, forced_image);
                 /* Default to "/", bail if it doesn't work. */
                 if (!boot_manager_set_prefix(manager, "/")) {
                         return false;
                 }
         }
 
-        if (forced_image) {
-                boot_manager_set_image_mode(manager, true);
-        } else {
-                /* Set the image mode */
-                boot_manager_set_image_mode(manager, image_mode);
-        }
-
         /* Let CBM take care of the rest */
         return boot_manager_update(manager);
 }