diff --git a/subsys/mgmt/mcumgr/grp/img_mgmt/Kconfig b/subsys/mgmt/mcumgr/grp/img_mgmt/Kconfig
index 81fc57d92385d32..4a43a748e906613 100644
--- a/subsys/mgmt/mcumgr/grp/img_mgmt/Kconfig
+++ b/subsys/mgmt/mcumgr/grp/img_mgmt/Kconfig
@@ -153,6 +153,38 @@ config MCUMGR_GRP_IMG_MUTEX
 	  can be used by applications to reset the image management state (useful if there are
 	  multiple ways that firmware updates can be loaded).
 
+choice MCUMGR_GRP_IMG_TOO_LARGE_CHECK
+	prompt "Image size check overhead"
+	default MCUMGR_GRP_IMG_TOO_LARGE_DISABLED
+	help
+	  MCUboot images should be limited to the maximum size that the bootloader can swap, in
+	  order to know this size, additional information is needed from the MCUboot
+	  configuration, otherwise an image can be uploaded that is too large for the bootloader
+	  to swap, this selects which method to use.
+
+	  Note: setting this to a non-disabled option will prevent uploading of padded and
+	  confirmed images, if support for that is required then this feature should be left as
+	  disabled.
+
+config MCUMGR_GRP_IMG_TOO_LARGE_DISABLED
+	bool "Disabled"
+	help
+	  Will not take MCUboot configuration into account when checking for maximum file size.
+
+config MCUMGR_GRP_IMG_TOO_LARGE_SYSBUILD
+	bool "Via Sysbuild from MCUboot configuration"
+	depends on ROM_END_OFFSET > 0
+	help
+	  Will use the image overhead size calculated during Sysbuild image configuration.
+
+config MCUMGR_GRP_IMG_TOO_LARGE_BOOTLOADER_INFO
+	bool "Via retention bootloader info"
+	depends on RETENTION_BOOTLOADER_INFO_OUTPUT_FUNCTION
+	help
+	  Will fetch the maximum image size from the bootloader info retention subsystem module.
+
+endchoice
+
 module = MCUMGR_GRP_IMG
 module-str = mcumgr_grp_img
 source "subsys/logging/Kconfig.template.log_config"
diff --git a/subsys/mgmt/mcumgr/grp/img_mgmt/src/zephyr_img_mgmt.c b/subsys/mgmt/mcumgr/grp/img_mgmt/src/zephyr_img_mgmt.c
index 303f112709a1e34..9ed3cab36dec39a 100644
--- a/subsys/mgmt/mcumgr/grp/img_mgmt/src/zephyr_img_mgmt.c
+++ b/subsys/mgmt/mcumgr/grp/img_mgmt/src/zephyr_img_mgmt.c
@@ -19,6 +19,11 @@
 
 #include <mgmt/mcumgr/grp/img_mgmt/img_mgmt_priv.h>
 
+#if defined(CONFIG_MCUMGR_GRP_IMG_TOO_LARGE_BOOTLOADER_INFO)
+#include <zephyr/retention/retention.h>
+#include <zephyr/retention/blinfo.h>
+#endif
+
 LOG_MODULE_DECLARE(mcumgr_img_grp, CONFIG_MCUMGR_GRP_IMG_LOG_LEVEL);
 
 #define SLOT0_PARTITION		slot0_partition
@@ -564,6 +569,18 @@ int img_mgmt_upload_inspect(const struct img_mgmt_upload_req *req,
 	if (req->off == 0) {
 		/* First upload chunk. */
 		const struct flash_area *fa;
+#if defined(CONFIG_MCUMGR_GRP_IMG_TOO_LARGE_SYSBUILD) &&			\
+	(defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_WITHOUT_SCRATCH) ||	\
+	 defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_SCRATCH) ||		\
+	 defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_OVERWRITE_ONLY) ||		\
+	 defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP) ||			\
+	 defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP_WITH_REVERT)) &&	\
+	CONFIG_MCUBOOT_UPDATE_FOOTER_SIZE > 0
+		const struct flash_area *fa_current;
+		int current_img_area;
+#elif defined(CONFIG_MCUMGR_GRP_IMG_TOO_LARGE_BOOTLOADER_INFO)
+		int max_image_size;
+#endif
 
 		if (req->img_data.len < sizeof(struct image_header)) {
 			/*  Image header is the first thing in the image */
@@ -576,6 +593,7 @@ int img_mgmt_upload_inspect(const struct img_mgmt_upload_req *req,
 			IMG_MGMT_UPLOAD_ACTION_SET_RC_RSN(action, img_mgmt_err_str_hdr_malformed);
 			return IMG_MGMT_ERR_INVALID_LENGTH;
 		}
+
 		action->size = req->size;
 
 		hdr = (struct image_header *)req->img_data.value;
@@ -626,6 +644,70 @@ int img_mgmt_upload_inspect(const struct img_mgmt_upload_req *req,
 			return IMG_MGMT_ERR_INVALID_IMAGE_TOO_LARGE;
 		}
 
+#if defined(CONFIG_MCUMGR_GRP_IMG_TOO_LARGE_SYSBUILD) &&		\
+	!defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SINGLE_APP) &&		\
+	!defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_FIRMWARE_UPDATER) &&	\
+	CONFIG_MCUBOOT_UPDATE_FOOTER_SIZE > 0
+
+//check if direct XIP (without revert) is needed
+#if defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_WITHOUT_SCRATCH) ||	\
+	defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_SCRATCH) ||		\
+	defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_OVERWRITE_ONLY) ||	\
+	defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP) ||		\
+	defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP_WITH_REVERT)
+		/* Check if slot1 is larger than slot0 by the update size, if so then the size
+		 * check can be skipped because the devicetree partitions are okay
+		 */
+		current_img_area = img_mgmt_flash_area_id(req->image);
+
+		rc = flash_area_open(current_img_area, &fa_current);
+		if (rc) {
+			IMG_MGMT_UPLOAD_ACTION_SET_RC_RSN(action,
+				img_mgmt_err_str_flash_open_failed);
+			LOG_ERR("Failed to open flash area ID %u: %d", current_img_area, rc);
+			flash_area_close(fa);
+			return IMG_MGMT_ERR_FLASH_OPEN_FAILED;
+		}
+
+		flash_area_close(fa_current);
+
+		LOG_DBG("Primary size: %d, secondary size: %d, overhead: %d, max update size: %d",
+			fa_current->fa_size, fa->fa_size, CONFIG_ROM_END_OFFSET,
+			(fa->fa_size + CONFIG_ROM_END_OFFSET));
+
+		if (fa_current->fa_size >= (fa->fa_size + CONFIG_ROM_END_OFFSET)) {
+			/* Upgrade slot is of sufficient size, nothing to check */
+			goto skip_size_check;
+		}
+#endif
+
+		if (req->size > (fa->fa_size - CONFIG_MCUBOOT_UPDATE_FOOTER_SIZE)) {
+			IMG_MGMT_UPLOAD_ACTION_SET_RC_RSN(action,
+				img_mgmt_err_str_image_too_large);
+			flash_area_close(fa);
+			LOG_ERR("Upload too large for slot (with end offset): %u > %u", req->size,
+				(fa->fa_size - CONFIG_ROM_END_OFFSET));
+			return IMG_MGMT_ERR_INVALID_IMAGE_TOO_LARGE;
+		}
+
+#if defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_WITHOUT_SCRATCH) || defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_SWAP_SCRATCH) || defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_OVERWRITE_ONLY) || defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP) || defined(CONFIG_MCUBOOT_BOOTLOADER_MODE_DIRECT_XIP_WITH_REVERT)
+skip_size_check:
+#endif
+#elif defined(CONFIG_MCUMGR_GRP_IMG_TOO_LARGE_BOOTLOADER_INFO)
+		rc = blinfo_lookup(BLINFO_MAX_APPLICATION_SIZE, (char *)&max_image_size,
+				   sizeof(max_image_size));
+
+		if (rc == sizeof(max_image_size) && max_image_size > 0 &&
+		    req->size > max_image_size) {
+			IMG_MGMT_UPLOAD_ACTION_SET_RC_RSN(action,
+				img_mgmt_err_str_image_too_large);
+			flash_area_close(fa);
+			LOG_ERR("Upload too large for slot (with max image size): %u > %u",
+				req->size, max_image_size);
+			return IMG_MGMT_ERR_INVALID_IMAGE_TOO_LARGE;
+		}
+#endif
+
 #if defined(CONFIG_MCUMGR_GRP_IMG_REJECT_DIRECT_XIP_MISMATCHED_SLOT)
 		if (hdr->ih_flags & IMAGE_F_ROM_FIXED) {
 			if (fa->fa_off != hdr->ih_load_addr) {