diff --git a/tools/cmake/UploadMethodManager.cmake b/tools/cmake/UploadMethodManager.cmake
index 0f6a2b2e356..d4288ba8ae5 100644
--- a/tools/cmake/UploadMethodManager.cmake
+++ b/tools/cmake/UploadMethodManager.cmake
@@ -146,4 +146,10 @@ function(mbed_generate_upload_target target)
 	else()
 		gen_upload_target(${target} ${CMAKE_CURRENT_BINARY_DIR}/$<TARGET_FILE_BASE_NAME:${target}>.hex)
 	endif()
+
+	# Make sure building the upload target causes the target to be built first
+	if(TARGET flash-${target})
+		add_dependencies(flash-${target} ${target})
+	endif()
+
 endfunction()
\ No newline at end of file
diff --git a/tools/cmake/upload_methods/FindLinkServer.cmake b/tools/cmake/upload_methods/FindLinkServer.cmake
index 5bbf90527ab..bb08b929b0c 100644
--- a/tools/cmake/upload_methods/FindLinkServer.cmake
+++ b/tools/cmake/upload_methods/FindLinkServer.cmake
@@ -7,6 +7,7 @@
 # This module defines:
 # LinkServer - Whether the reqested tools were found.
 # LinkServer_PATH - full path to the LinkServer command line tool.
+# LinkServer_VERSION - version number of LinkServer
 
 # Check for LinkServer install folders on Windows
 if("${CMAKE_HOST_SYSTEM_NAME}" STREQUAL "Windows")
@@ -26,6 +27,16 @@ find_program(LinkServer_PATH
     HINTS ${LINKSERVER_HINTS}
 )
 
-find_package_handle_standard_args(LinkServer REQUIRED_VARS LinkServer_PATH)
+if(EXISTS "${LinkServer_PATH}")
+	# Detect version
+	execute_process(COMMAND ${LinkServer_PATH} --version
+			OUTPUT_VARIABLE LinkServer_VERSION_OUTPUT)
+
+	# The output looks like "LinkServer v1.2.45 [Build 45] [2023-07-25 09:54:50]", so use a regex to grab the version
+	string(REGEX REPLACE "LinkServer v([0-9]+\\.[0-9]+\\.[0-9]+).*" "\\1" LinkServer_VERSION ${LinkServer_VERSION_OUTPUT})
+endif()
+
+
+find_package_handle_standard_args(LinkServer REQUIRED_VARS LinkServer_PATH VERSION_VAR LinkServer_VERSION)
 
 
diff --git a/tools/cmake/upload_methods/UploadMethodARDUINO_BOSSAC.cmake b/tools/cmake/upload_methods/UploadMethodARDUINO_BOSSAC.cmake
index ca9a5c2a639..526d6975b5a 100644
--- a/tools/cmake/upload_methods/UploadMethodARDUINO_BOSSAC.cmake
+++ b/tools/cmake/upload_methods/UploadMethodARDUINO_BOSSAC.cmake
@@ -28,6 +28,4 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		--write ${BINARY_FILE}
 		--reset)
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
-
 endfunction(gen_upload_target)
diff --git a/tools/cmake/upload_methods/UploadMethodJLINK.cmake b/tools/cmake/upload_methods/UploadMethodJLINK.cmake
index 19b06a21b6b..11ae4c78046 100644
--- a/tools/cmake/upload_methods/UploadMethodJLINK.cmake
+++ b/tools/cmake/upload_methods/UploadMethodJLINK.cmake
@@ -71,9 +71,6 @@ exit
 		-ExitOnError
 		-CommandFile ${COMMAND_FILE_PATH})
 
-
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
-
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.
diff --git a/tools/cmake/upload_methods/UploadMethodLINKSERVER.cmake b/tools/cmake/upload_methods/UploadMethodLINKSERVER.cmake
index edc46a76040..5ee41ed2765 100644
--- a/tools/cmake/upload_methods/UploadMethodLINKSERVER.cmake
+++ b/tools/cmake/upload_methods/UploadMethodLINKSERVER.cmake
@@ -23,6 +23,12 @@ endif()
 find_package(LinkServer)
 set(UPLOAD_LINKSERVER_FOUND ${LinkServer_FOUND})
 
+if(LinkServer_FOUND)
+	if(${LinkServer_VERSION} VERSION_LESS 1.5.30 AND "${MBED_OUTPUT_EXT}" STREQUAL "hex")
+		message(FATAL_ERROR "LinkServer <1.5.30 does not support flashing hex files! Please upgrade LinkServer and then clean and rebuild the project.")
+	endif()
+endif()
+
 ### Function to generate upload target
 
 function(gen_upload_target TARGET_NAME BINARY_FILE)
@@ -37,8 +43,6 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 			--addr ${MBED_UPLOAD_BASE_ADDR}
 			${BINARY_FILE})
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
-
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.
diff --git a/tools/cmake/upload_methods/UploadMethodMBED.cmake b/tools/cmake/upload_methods/UploadMethodMBED.cmake
index 654a6c26705..e1e11ca2c3a 100644
--- a/tools/cmake/upload_methods/UploadMethodMBED.cmake
+++ b/tools/cmake/upload_methods/UploadMethodMBED.cmake
@@ -25,6 +25,4 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 			${mbed-os_SOURCE_DIR}/tools/python
 		VERBATIM)
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
-
 endfunction(gen_upload_target)
diff --git a/tools/cmake/upload_methods/UploadMethodOPENOCD.cmake b/tools/cmake/upload_methods/UploadMethodOPENOCD.cmake
index 34f6fed9fdc..61d2b09adaa 100644
--- a/tools/cmake/upload_methods/UploadMethodOPENOCD.cmake
+++ b/tools/cmake/upload_methods/UploadMethodOPENOCD.cmake
@@ -41,7 +41,6 @@ endif()
 
 function(gen_upload_target TARGET_NAME BINARY_FILE)
 
-	# unlike other upload methods, OpenOCD uses the elf file
 	add_custom_target(flash-${TARGET_NAME}
 		COMMENT "Flashing ${TARGET_NAME} with OpenOCD..."
 		COMMAND ${OpenOCD}
@@ -51,7 +50,6 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		-c "program ${BINARY_FILE} ${MBED_UPLOAD_BASE_ADDR} reset exit"
 		VERBATIM)
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.
diff --git a/tools/cmake/upload_methods/UploadMethodPICOTOOL.cmake b/tools/cmake/upload_methods/UploadMethodPICOTOOL.cmake
index 340ae768676..aad1ed715d0 100644
--- a/tools/cmake/upload_methods/UploadMethodPICOTOOL.cmake
+++ b/tools/cmake/upload_methods/UploadMethodPICOTOOL.cmake
@@ -29,12 +29,16 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		list(APPEND PICOTOOL_TARGET_ARGS --address ${PICOTOOL_TARGET_ADDRESS})
 	endif()
 
+	if("${MBED_OUTPUT_EXT}" STREQUAL "hex")
+        message(FATAL_ERROR "Bin file output must be enabled to use picotool.  Set MBED_OUTPUT_EXT to empty string or to 'bin' in your top level CMakeLists.txt!")
+    endif()
+
 	add_custom_target(flash-${TARGET_NAME}
 		COMMAND ${Picotool}
 			load
+			--verify
 		    --execute
-			$<TARGET_FILE:${TARGET_NAME}>)
-
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
+			--offset ${MBED_UPLOAD_BASE_ADDR}
+			${CMAKE_CURRENT_BINARY_DIR}/$<TARGET_FILE_BASE_NAME:${TARGET_NAME}>.bin)
 
 endfunction(gen_upload_target)
diff --git a/tools/cmake/upload_methods/UploadMethodPYOCD.cmake b/tools/cmake/upload_methods/UploadMethodPYOCD.cmake
index 848b54bdd69..ad6d947a349 100644
--- a/tools/cmake/upload_methods/UploadMethodPYOCD.cmake
+++ b/tools/cmake/upload_methods/UploadMethodPYOCD.cmake
@@ -34,7 +34,6 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		--base-address ${MBED_UPLOAD_BASE_ADDR}
 		${BINARY_FILE})
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.
diff --git a/tools/cmake/upload_methods/UploadMethodSTLINK.cmake b/tools/cmake/upload_methods/UploadMethodSTLINK.cmake
index a7a40117d88..872af59ae66 100644
--- a/tools/cmake/upload_methods/UploadMethodSTLINK.cmake
+++ b/tools/cmake/upload_methods/UploadMethodSTLINK.cmake
@@ -32,7 +32,6 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		${STLINK_ARGS}
 		write ${BINARY_FILE} ${MBED_UPLOAD_BASE_ADDR})
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.
diff --git a/tools/cmake/upload_methods/UploadMethodSTM32CUBE.cmake b/tools/cmake/upload_methods/UploadMethodSTM32CUBE.cmake
index f6229fe8776..04561abdb67 100644
--- a/tools/cmake/upload_methods/UploadMethodSTM32CUBE.cmake
+++ b/tools/cmake/upload_methods/UploadMethodSTM32CUBE.cmake
@@ -36,8 +36,6 @@ function(gen_upload_target TARGET_NAME BINARY_FILE)
 		-w ${BINARY_FILE} ${MBED_UPLOAD_BASE_ADDR}
 		-rst)
 
-	add_dependencies(flash-${TARGET_NAME} ${TARGET_NAME})
-
 endfunction(gen_upload_target)
 
 ### Commands to run the debug server.