diff --git a/src/plugins/mcusupport/mcusupportsdk.cpp b/src/plugins/mcusupport/mcusupportsdk.cpp
index cd12a616138..83655ab34fb 100644
--- a/src/plugins/mcusupport/mcusupportsdk.cpp
+++ b/src/plugins/mcusupport/mcusupportsdk.cpp
@@ -368,8 +368,8 @@ McuPackagePtr createStm32CubeProgrammerPackage(const SettingsHandler::Ptr &setti
         FilePath defaultPath = {};
 
     const FilePath detectionPath = FilePath::fromUserInput(
-        QLatin1String(Utils::HostOsInfo::isWindowsHost() ? "/bin/STM32_Programmer_CLI.exe"
-                                                         : "/bin/STM32_Programmer.sh"));
+        QLatin1String(Utils::HostOsInfo::isWindowsHost() ? "bin/STM32_Programmer_CLI.exe"
+                                                         : "bin/STM32_Programmer.sh"));
 
     return McuPackagePtr{
         new McuPackage(settingsHandler,
@@ -617,6 +617,16 @@ VersionDetection parseVersionDetection(const QJsonObject &packageEntry)
     };
 }
 
+QString getOsSpecificValue(const QJsonValue &entry)
+{
+    if (entry.isObject()) {
+        //The json entry has os-specific values
+        return entry[HostOsInfo::isWindowsHost() ? QString("windows") : QString("linux")].toString();
+    }
+    //The entry does not have os-specific values
+    return entry.toString();
+}
+
 static PackageDescription parsePackage(const QJsonObject &cmakeEntry)
 {
     const QVariantList versionsVariantList = cmakeEntry["versions"].toArray().toVariantList();
@@ -626,14 +636,8 @@ static PackageDescription parsePackage(const QJsonObject &cmakeEntry)
                                                         });
 
     //Parse the default value depending on the operating system
-    QString defaultPathString;
-    if (cmakeEntry["defaultValue"].isObject())
-        defaultPathString
-            = cmakeEntry["defaultValue"]
-                  .toObject()[HostOsInfo::isWindowsHost() ? QString("windows") : QString("unix")]
-                  .toString("");
-    else
-        defaultPathString = cmakeEntry["defaultValue"].toString();
+    QString defaultPathString = getOsSpecificValue(cmakeEntry["defaultValue"]);
+    QString detectionPathString = getOsSpecificValue(cmakeEntry["detectionPath"]);
 
     return {cmakeEntry["label"].toString(),
             cmakeEntry["envVar"].toString(),
@@ -641,7 +645,7 @@ static PackageDescription parsePackage(const QJsonObject &cmakeEntry)
             cmakeEntry["description"].toString(),
             cmakeEntry["setting"].toString(),
             FilePath::fromUserInput(defaultPathString),
-            FilePath::fromUserInput(cmakeEntry["validation"].toString()),
+            FilePath::fromUserInput(detectionPathString),
             versions,
             parseVersionDetection(cmakeEntry),
             cmakeEntry["addToSystemPath"].toBool()};
diff --git a/src/plugins/mcusupport/mcutargetdescription.h b/src/plugins/mcusupport/mcutargetdescription.h
index 8dd510af81c..3b811e5a034 100644
--- a/src/plugins/mcusupport/mcutargetdescription.h
+++ b/src/plugins/mcusupport/mcutargetdescription.h
@@ -29,7 +29,7 @@ struct PackageDescription
     QString description;
     QString setting;
     Utils::FilePath defaultPath;
-    Utils::FilePath validationPath;
+    Utils::FilePath detectionPath;
     QStringList versions;
     VersionDetection versionDetection;
     bool shouldAddToSystemPath;
diff --git a/src/plugins/mcusupport/mcutargetfactory.cpp b/src/plugins/mcusupport/mcutargetfactory.cpp
index b7a8cffd054..00a81450274 100644
--- a/src/plugins/mcusupport/mcutargetfactory.cpp
+++ b/src/plugins/mcusupport/mcutargetfactory.cpp
@@ -131,7 +131,7 @@ McuPackagePtr McuTargetFactory::createPackage(const PackageDescription &pkgDesc)
     return McuPackagePtr{new McuPackage{settingsHandler,
                                         pkgDesc.label,
                                         pkgDesc.defaultPath,
-                                        pkgDesc.validationPath,
+                                        pkgDesc.detectionPath,
                                         pkgDesc.setting,
                                         pkgDesc.cmakeVar,
                                         pkgDesc.envVar,
@@ -166,7 +166,7 @@ McuToolChainPackage *McuTargetFactory::createToolchain(
         return new McuToolChainPackage{settingsHandler,
                                        compilerDescription.label,
                                        compilerDescription.defaultPath,
-                                       compilerDescription.validationPath,
+                                       compilerDescription.detectionPath,
                                        {},
                                        toolchainType,
                                        toolchain.versions,
@@ -206,7 +206,7 @@ McuToolChainPackage *McuTargetFactory::createToolchain(
     return new McuToolChainPackage{settingsHandler,
                                    compilerDescription.label,
                                    compilerDescription.defaultPath,
-                                   compilerDescription.validationPath,
+                                   compilerDescription.detectionPath,
                                    compilerDescription.setting,
                                    toolchainType,
                                    toolchain.versions,
diff --git a/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_baremetal_json.h
index 92b3c733dab..479074d01d8 100644
--- a/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_baremetal_json.h
@@ -22,7 +22,7 @@ constexpr auto armgcc_ek_ra6m3g_baremetal_json = R"(
                 "type": "path",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/SEGGER/JLink",
-                    "unix": "/opt/SEGGER/JLink"
+                    "linux": "/opt/SEGGER/JLink"
                 },
                 "optional": true,
                 "addToSystemPath": true
@@ -46,6 +46,10 @@ constexpr auto armgcc_ek_ra6m3g_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_freertos_json.h b/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_freertos_json.h
index e347828d093..578f3071e05 100644
--- a/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_freertos_json.h
+++ b/src/plugins/mcusupport/test/armgcc_ek_ra6m3g_freertos_json.h
@@ -22,7 +22,7 @@ constexpr auto armgcc_ek_ra6m3g_freertos_json = R"(
                 "type": "path",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/SEGGER/JLink",
-                    "unix": "/opt/SEGGER/JLink"
+                    "linux": "/opt/SEGGER/JLink"
                 },
                 "optional": true,
                 "addToSystemPath": true
@@ -46,6 +46,10 @@ constexpr auto armgcc_ek_ra6m3g_freertos_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
@@ -74,7 +78,7 @@ constexpr auto armgcc_ek_ra6m3g_freertos_json = R"(
         "label": "FreeRTOS SDK for EK-RA6M3G",
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{Qul_ROOT}/platform/boards/renesas/ek-ra6m3g-common/3rdparty/freertos",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "optional": false
     }
diff --git a/src/plugins/mcusupport/test/armgcc_example_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_example_baremetal_json.h
index 0e1bc9ca461..a72af967c6e 100644
--- a/src/plugins/mcusupport/test/armgcc_example_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_example_baremetal_json.h
@@ -31,6 +31,10 @@ constexpr auto armgcc_example_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_baremetal_json.h
index a6a6fc2f796..21e154cbde1 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_baremetal_json.h
@@ -22,10 +22,11 @@ constexpr auto armgcc_mimxrt1050_evk_baremetal_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -49,6 +50,10 @@ constexpr auto armgcc_mimxrt1050_evk_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_freertos_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_freertos_json.h
index 1d3eb8eeb23..b366a3f0167 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1050_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto armgcc_mimxrt1050_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -49,6 +50,10 @@ constexpr auto armgcc_mimxrt1050_evk_freertos_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
@@ -80,7 +85,7 @@ constexpr auto armgcc_mimxrt1050_evk_freertos_json = R"(
     "freeRTOS": {
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "envVar": "IMXRT1050_FREERTOS_DIR",
         "label": "FreeRTOS SDK for MIMXRT1050-EVK",
         "optional": false,
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1060_evk_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1060_evk_baremetal_json.h
index f8a164cdf33..efe74d094e7 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1060_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1060_evk_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto armgcc_mimxrt1060_evk_baremetal_json = R"(
                 "cmakeVar": "MCUXPRESSO_IDE_PATH",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
+                },
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -45,6 +49,10 @@ constexpr auto armgcc_mimxrt1060_evk_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_baremetal_json.h
index 21d760fb13e..e8c71e5292d 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_baremetal_json.h
@@ -22,10 +22,11 @@ constexpr auto armgcc_mimxrt1064_evk_baremetal_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -49,6 +50,10 @@ constexpr auto armgcc_mimxrt1064_evk_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_freertos_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_freertos_json.h
index e0b6ae8db10..138a7a56eb7 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1064_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto armgcc_mimxrt1064_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -49,6 +50,10 @@ constexpr auto armgcc_mimxrt1064_evk_freertos_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
@@ -80,7 +85,7 @@ constexpr auto armgcc_mimxrt1064_evk_freertos_json = R"(
     "freeRTOS": {
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "envVar": "IMXRT1064_FREERTOS_DIR",
         "label": "FreeRTOS SDK for MIMXRT1064-EVK",
         "optional": false,
diff --git a/src/plugins/mcusupport/test/armgcc_mimxrt1170_evk_freertos_json.h b/src/plugins/mcusupport/test/armgcc_mimxrt1170_evk_freertos_json.h
index 23407137161..5aab5105bcb 100644
--- a/src/plugins/mcusupport/test/armgcc_mimxrt1170_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/armgcc_mimxrt1170_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto armgcc_mimxrt1170_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -49,6 +50,10 @@ constexpr auto armgcc_mimxrt1170_evk_freertos_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
@@ -81,7 +86,7 @@ constexpr auto armgcc_mimxrt1170_evk_freertos_json = R"(
         "envVar": "EVK_MIMXRT1170_FREERTOS_PATH",
         "label": "FreeRTOS SDK for MIMXRT1170-EVK",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "optional": false
     }
diff --git a/src/plugins/mcusupport/test/armgcc_stm32f469i_discovery_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_stm32f469i_discovery_baremetal_json.h
index 27f8a85d96d..4d945ededc3 100644
--- a/src/plugins/mcusupport/test/armgcc_stm32f469i_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_stm32f469i_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto armgcc_stm32f469i_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -45,6 +49,10 @@ constexpr auto armgcc_stm32f469i_discovery_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_baremetal_json.h
index 405c25f934a..a748335707b 100644
--- a/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto armgcc_stm32f769i_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -45,6 +49,10 @@ constexpr auto armgcc_stm32f769i_discovery_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_freertos_json.h b/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_freertos_json.h
index c061bd19e8b..3d3acd05e07 100644
--- a/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_freertos_json.h
+++ b/src/plugins/mcusupport/test/armgcc_stm32f769i_discovery_freertos_json.h
@@ -21,7 +21,11 @@ constexpr auto armgcc_stm32f769i_discovery_freertos_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -45,6 +49,10 @@ constexpr auto armgcc_stm32f769i_discovery_freertos_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
@@ -78,7 +86,7 @@ constexpr auto armgcc_stm32f769i_discovery_freertos_json = R"(
         "label": "FreeRTOS SDK for STM32F769I-Discovery",
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/Middlewares/Third_Party/FreeRTOS/Source",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "setting": "FreeRTOSSourcePackage_STM32F7",
         "optional": false
diff --git a/src/plugins/mcusupport/test/armgcc_stm32h750b_discovery_baremetal_json.h b/src/plugins/mcusupport/test/armgcc_stm32h750b_discovery_baremetal_json.h
index 66af227d7b0..922f444ce66 100644
--- a/src/plugins/mcusupport/test/armgcc_stm32h750b_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/armgcc_stm32h750b_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto armgcc_stm32h750b_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -45,6 +49,10 @@ constexpr auto armgcc_stm32h750b_discovery_baremetal_json = R"(
                 "filePattern": "bin/arm-none-eabi-g++",
                 "executableArgs": "--version",
                 "regex": "\\bv(\\d+\\.\\d+\\.\\d+)\\b"
+            },
+            "detectionPath": {
+                "windows": "bin/arm-none-eabi-g++.exe",
+                "linux": "bin/arm-none-eabi-g++"
             }
         },
         "file": {
diff --git a/src/plugins/mcusupport/test/errors_json.h b/src/plugins/mcusupport/test/errors_json.h
index 9ab54ed68a7..ce74f5d90c0 100644
--- a/src/plugins/mcusupport/test/errors_json.h
+++ b/src/plugins/mcusupport/test/errors_json.h
@@ -91,7 +91,7 @@ constexpr auto mulitple_toolchain_versions = R"(
         "setting": "Stm32CubeProgrammer",
         "defaultValue": {
           "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-          "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+          "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
         },
         "optional": false
       }
diff --git a/src/plugins/mcusupport/test/ghs_rh850_d1m1a_baremetal_json.h b/src/plugins/mcusupport/test/ghs_rh850_d1m1a_baremetal_json.h
index 40127e894f0..32422dc5f2e 100644
--- a/src/plugins/mcusupport/test/ghs_rh850_d1m1a_baremetal_json.h
+++ b/src/plugins/mcusupport/test/ghs_rh850_d1m1a_baremetal_json.h
@@ -23,7 +23,11 @@ constexpr auto ghs_rh850_d1m1a_baremetal_json = R"(
                 "cmakeVar": "RENESAS_FLASH_PROGRAMMER_PATH",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/Renesas Electronics/Programming Tools/Renesas Flash Programmer V3.09",
-                    "unix": "%{Env:HOME}"
+                    "linux": "%{Env:HOME}"
+                },
+                "detectionPath": {
+                    "windows": "rfp-cli.exe",
+                    "linux": "rfp-cli"
                 },
                 "envVar": "RENESAS_FLASH_PROGRAMMER_PATH",
                 "optional": true,
diff --git a/src/plugins/mcusupport/test/iar_ek_ra6m3g_baremetal_json.h b/src/plugins/mcusupport/test/iar_ek_ra6m3g_baremetal_json.h
index 3df8455c07d..c612bd42ebd 100644
--- a/src/plugins/mcusupport/test/iar_ek_ra6m3g_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_ek_ra6m3g_baremetal_json.h
@@ -22,7 +22,7 @@ constexpr auto iar_ek_ra6m3g_baremetal_json = R"(
                 "type": "path",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/SEGGER/JLink",
-                    "unix": "/opt/SEGGER/JLink"
+                    "linux": "/opt/SEGGER/JLink"
                 },
                 "optional": true,
                 "addToSystemPath": true
@@ -45,7 +45,12 @@ constexpr auto iar_ek_ra6m3g_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_ek_ra6m3g_freertos_json.h b/src/plugins/mcusupport/test/iar_ek_ra6m3g_freertos_json.h
index 570259672cf..98ebfbb4b1c 100644
--- a/src/plugins/mcusupport/test/iar_ek_ra6m3g_freertos_json.h
+++ b/src/plugins/mcusupport/test/iar_ek_ra6m3g_freertos_json.h
@@ -22,7 +22,7 @@ constexpr auto iar_ek_ra6m3g_freertos_json = R"(
                 "type": "path",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/SEGGER/JLink",
-                    "unix": "/opt/SEGGER/JLink"
+                    "linux": "/opt/SEGGER/JLink"
                 },
                 "optional": true,
                 "addToSystemPath": true
@@ -45,7 +45,12 @@ constexpr auto iar_ek_ra6m3g_freertos_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
@@ -73,7 +78,7 @@ constexpr auto iar_ek_ra6m3g_freertos_json = R"(
         "label": "FreeRTOS SDK for EK-RA6M3G",
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{Qul_ROOT}/platform/boards/renesas/ek-ra6m3g-common/3rdparty/freertos",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "optional": false
     }
diff --git a/src/plugins/mcusupport/test/iar_example_baremetal_json.h b/src/plugins/mcusupport/test/iar_example_baremetal_json.h
index ca73ea8b422..66e6abde63c 100644
--- a/src/plugins/mcusupport/test/iar_example_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_example_baremetal_json.h
@@ -30,7 +30,12 @@ constexpr auto iar_example_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1050_evk_baremetal_json.h b/src/plugins/mcusupport/test/iar_mimxrt1050_evk_baremetal_json.h
index 9903abd6c84..5fe5a089842 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1050_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1050_evk_baremetal_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1050_evk_baremetal_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1050_evk_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1050_evk_freertos_json.h b/src/plugins/mcusupport/test/iar_mimxrt1050_evk_freertos_json.h
index c5c0cee2d4c..93d23e305a2 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1050_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1050_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1050_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1050_evk_freertos_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
@@ -79,7 +85,7 @@ constexpr auto iar_mimxrt1050_evk_freertos_json = R"(
     "freeRTOS": {
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "envVar": "IMXRT1050_FREERTOS_DIR",
         "label": "FreeRTOS SDK for MIMXRT1050-EVK",
         "optional": false,
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1060_evk_baremetal_json.h b/src/plugins/mcusupport/test/iar_mimxrt1060_evk_baremetal_json.h
index 5ad87a16c56..6600150f5d6 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1060_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1060_evk_baremetal_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1060_evk_baremetal_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1060_evk_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1064_evk_baremetal_json.h b/src/plugins/mcusupport/test/iar_mimxrt1064_evk_baremetal_json.h
index 634d3b92505..83d3c23b1a9 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1064_evk_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1064_evk_baremetal_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1064_evk_baremetal_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1064_evk_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1064_evk_freertos_json.h b/src/plugins/mcusupport/test/iar_mimxrt1064_evk_freertos_json.h
index 8a223c2a6db..2f71e359048 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1064_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1064_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1064_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1064_evk_freertos_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
@@ -79,7 +85,7 @@ constexpr auto iar_mimxrt1064_evk_freertos_json = R"(
     "freeRTOS": {
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "envVar": "IMXRT1064_FREERTOS_DIR",
         "label": "FreeRTOS SDK for MIMXRT1064-EVK",
         "optional": false,
diff --git a/src/plugins/mcusupport/test/iar_mimxrt1170_evk_freertos_json.h b/src/plugins/mcusupport/test/iar_mimxrt1170_evk_freertos_json.h
index c77aa9c3f32..4143e88cd65 100644
--- a/src/plugins/mcusupport/test/iar_mimxrt1170_evk_freertos_json.h
+++ b/src/plugins/mcusupport/test/iar_mimxrt1170_evk_freertos_json.h
@@ -22,10 +22,11 @@ constexpr auto iar_mimxrt1170_evk_freertos_json = R"(
                 "setting": "MCUXpressoIDE",
                 "defaultValue": {
                     "windows": "%{Env:ROOT}/nxp/MCUXpressoIDE*",
-                    "unix": "/usr/local/mcuxpressoide/"
+                    "linux": "/usr/local/mcuxpressoide/"
                 },
-                "versionDetection": {
-                    "filePattern": "ide/binaries/crt_emu_cm_redlink"
+                "detectionPath": {
+                    "windows": "ide/binaries/crt_emu_cm_redlink.exe",
+                    "linux": "ide/binaries/crt_emu_cm_redlink"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -48,7 +49,12 @@ constexpr auto iar_mimxrt1170_evk_freertos_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
@@ -80,7 +86,7 @@ constexpr auto iar_mimxrt1170_evk_freertos_json = R"(
         "envVar": "EVK_MIMXRT1170_FREERTOS_PATH",
         "label": "FreeRTOS SDK for MIMXRT1170-EVK",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/rtos/freertos/freertos_kernel",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "optional": false
     }
diff --git a/src/plugins/mcusupport/test/iar_stm32f469i_discovery_baremetal_json.h b/src/plugins/mcusupport/test/iar_stm32f469i_discovery_baremetal_json.h
index 6b1edf70b0d..c5b2c4cba60 100644
--- a/src/plugins/mcusupport/test/iar_stm32f469i_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_stm32f469i_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto iar_stm32f469i_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -44,7 +48,12 @@ constexpr auto iar_stm32f469i_discovery_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_stm32f769i_discovery_baremetal_json.h b/src/plugins/mcusupport/test/iar_stm32f769i_discovery_baremetal_json.h
index 8ff4c748cde..5ac1c9f67df 100644
--- a/src/plugins/mcusupport/test/iar_stm32f769i_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_stm32f769i_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto iar_stm32f769i_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -44,7 +48,12 @@ constexpr auto iar_stm32f769i_discovery_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_stm32f769i_discovery_freertos_json.h b/src/plugins/mcusupport/test/iar_stm32f769i_discovery_freertos_json.h
index 2817aed3a0d..19e77fd5e08 100644
--- a/src/plugins/mcusupport/test/iar_stm32f769i_discovery_freertos_json.h
+++ b/src/plugins/mcusupport/test/iar_stm32f769i_discovery_freertos_json.h
@@ -21,7 +21,11 @@ constexpr auto iar_stm32f769i_discovery_freertos_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -44,7 +48,12 @@ constexpr auto iar_stm32f769i_discovery_freertos_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
@@ -77,7 +86,7 @@ constexpr auto iar_stm32f769i_discovery_freertos_json = R"(
         "label": "FreeRTOS SDK for STM32F769I-Discovery",
         "cmakeVar": "FREERTOS_DIR",
         "defaultValue": "%{QUL_BOARD_SDK_DIR}/Middlewares/Third_Party/FreeRTOS/Source",
-        "validation": "tasks.c",
+        "detectionPath": "tasks.c",
         "type": "path",
         "setting": "FreeRTOSSourcePackage_STM32F7",
         "optional": false
diff --git a/src/plugins/mcusupport/test/iar_stm32h750b_discovery_baremetal_json.h b/src/plugins/mcusupport/test/iar_stm32h750b_discovery_baremetal_json.h
index 836cdde05d0..ae76ca9bd15 100644
--- a/src/plugins/mcusupport/test/iar_stm32h750b_discovery_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_stm32h750b_discovery_baremetal_json.h
@@ -21,7 +21,11 @@ constexpr auto iar_stm32h750b_discovery_baremetal_json = R"(
                 "setting": "Stm32CubeProgrammer",
                 "defaultValue": {
                     "windows": "%{Env:PROGRAMSANDFILES}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/",
-                    "unix": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                    "linux": "%{Env:HOME}/STMicroelectronics/STM32Cube/STM32CubeProgrammer/"
+                },
+                "detectionPath": {
+                    "windows": "bin/STM32_Programmer_CLI.exe",
+                    "linux": "bin/STM32_Programmer.sh"
                 },
                 "optional": false,
                 "addToSystemPath": true
@@ -44,7 +48,12 @@ constexpr auto iar_stm32h750b_discovery_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath": {
+                "windows": "bin/iccarm.exe",
+                "linux": "bin/iccarm"
+            },
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/iar_tviic2d6m_baremetal_json.h b/src/plugins/mcusupport/test/iar_tviic2d6m_baremetal_json.h
index 2b5ec845bf4..0e4d7442dfb 100644
--- a/src/plugins/mcusupport/test/iar_tviic2d6m_baremetal_json.h
+++ b/src/plugins/mcusupport/test/iar_tviic2d6m_baremetal_json.h
@@ -40,7 +40,9 @@ constexpr auto iar_tviic2d6m_baremetal_json = R"(
                 "filePattern": "bin/iccarm",
                 "executableArgs": "--version",
                 "regex": "\\bV(\\d+\\.\\d+\\.\\d+)\\.\\d+\\b"
-            }
+            },
+            "detectionPath":  "bin/iccarm.exe",
+            "optional": false
         },
         "file": {
             "id": "IAR_CMAKE_TOOLCHAIN_FILE",
diff --git a/src/plugins/mcusupport/test/unittest.cpp b/src/plugins/mcusupport/test/unittest.cpp
index d503489aae9..6d8e84c7979 100644
--- a/src/plugins/mcusupport/test/unittest.cpp
+++ b/src/plugins/mcusupport/test/unittest.cpp
@@ -132,18 +132,21 @@ const char xpressoIdeLabel[]{"MCUXpresso IDE"};
 const char xpressoIdeSetting[]{"MCUXpressoIDE"};
 const char xpressoIdeCmakeVar[]{"MCUXPRESSO_IDE_PATH"};
 const char xpressoIdeEnvVar[]{"MCUXpressoIDE_PATH"};
-const char xpressoIdeDetectionPath[]{"ide/binaries/crt_emu_cm_redlink"};
+const QString xpressoIdeDetectionPath{
+    HostOsInfo::withExecutableSuffix("ide/binaries/crt_emu_cm_redlink")};
 
 const char stmCubeProgrammerSetting[]{"Stm32CubeProgrammer"};
 const char stmCubeProgrammerLabel[]{"STM32CubeProgrammer"};
 const QString stmCubeProgrammerPath{QString{defaultToolPath} + "/bin"};
-const QString stmCubeProgrammerDetectionPath{"/bin/STM32_Programmer.sh"};
+const QString stmCubeProgrammerDetectionPath{HostOsInfo::isWindowsHost()
+                                                 ? QString("bin/STM32_Programmer_CLI.exe")
+                                                 : QString("bin/STM32_Programmer.sh")};
 
 const char renesasProgrammerSetting[]{"RenesasFlashProgrammer"};
 const char renesasProgrammerCmakeVar[]{"RENESAS_FLASH_PROGRAMMER_PATH"};
 const QString renesasProgrammerEnvVar{renesasProgrammerCmakeVar};
 const char renesasProgrammerLabel[]{"Renesas Flash Programmer"};
-const char renesasProgrammerDetectionPath[]{"rfp-cli"};
+const QString renesasProgrammerDetectionPath{HostOsInfo::withExecutableSuffix("rfp-cli")};
 
 const char renesasE2StudioCmakeVar[]{"EK_RA6M3G_E2_PROJECT_PATH"};
 const char renesasE2StudioDefaultPath[]{"%{Env:HOME}/e2_studio/workspace"};
@@ -155,7 +158,7 @@ const char cypressProgrammerSetting[]{"CypressAutoFlashUtil"};
 const char cypressProgrammerCmakeVar[]{"INFINEON_AUTO_FLASH_UTILITY_DIR"};
 const char cypressProgrammerEnvVar[]{"CYPRESS_AUTO_FLASH_UTILITY_DIR"};
 const char cypressProgrammerLabel[]{"Cypress Auto Flash Utility"};
-const char cypressProgrammerDetectionPath[]{"/bin/openocd"};
+const QString cypressProgrammerDetectionPath{HostOsInfo::withExecutableSuffix("/bin/openocd")};
 
 const char jlinkPath[]{"/opt/SEGGER/JLink"};
 const char jlinkSetting[]{"JLinkPath"};
@@ -1527,6 +1530,7 @@ void McuSupportTest::test_createThirdPartyPackage()
     QFETCH(QString, cmakeVar);
     QFETCH(QString, envVar);
     QFETCH(QString, label);
+    QFETCH(QString, detectionPath);
 
     McuTargetDescription targetDescription{parseDescriptionJson(json.toLocal8Bit())};
 
@@ -1544,7 +1548,15 @@ void McuSupportTest::test_createThirdPartyPackage()
         return (pkg->settingsKey() == setting);
     });
 
-    verifyPackage(thirdPartyPackage, path, defaultPath, setting, cmakeVar, envVar, label, {}, {});
+    verifyPackage(thirdPartyPackage,
+                  path,
+                  defaultPath,
+                  setting,
+                  cmakeVar,
+                  envVar,
+                  label,
+                  detectionPath,
+                  {});
 }
 
 void McuSupportTest::test_legacy_createCypressProgrammer3rdPartyPackage()
@@ -1594,15 +1606,20 @@ void McuSupportTest::test_createJLink3rdPartyPackage()
                   {});
 }
 
-void McuSupportTest::test_defaultValueForEachOperationSystem()
+void McuSupportTest::test_differentValueForEachOperationSystem()
 {
     const auto packageDescription = parseDescriptionJson(armgcc_mimxrt1050_evk_freertos_json);
     auto default_path_entry = packageDescription.platform.entries[0].defaultPath.toString();
+    auto validation_path_entry = packageDescription.platform.entries[0].detectionPath.toString();
 
-    if (HostOsInfo::isWindowsHost())
+    //TODO: Revisit whether this test is required and not currently covered by the third party packages
+    if (HostOsInfo::isWindowsHost()) {
         QCOMPARE(QString("%{Env:ROOT}/nxp/MCUXpressoIDE*"), default_path_entry);
-    else
+        QCOMPARE(QString("ide/binaries/crt_emu_cm_redlink.exe"), validation_path_entry);
+    } else {
         QCOMPARE(QString("/usr/local/mcuxpressoide"), default_path_entry);
+        QCOMPARE(QString("ide/binaries/crt_emu_cm_redlink"), validation_path_entry);
+    }
 };
 void McuSupportTest::test_addToSystemPathFlag()
 {
diff --git a/src/plugins/mcusupport/test/unittest.h b/src/plugins/mcusupport/test/unittest.h
index fae8fca93a7..25982d71bd3 100644
--- a/src/plugins/mcusupport/test/unittest.h
+++ b/src/plugins/mcusupport/test/unittest.h
@@ -100,7 +100,7 @@ private slots:
     void test_legacy_createCypressProgrammer3rdPartyPackage();
     void test_createJLink3rdPartyPackage();
 
-    void test_defaultValueForEachOperationSystem();
+    void test_differentValueForEachOperationSystem();
     void test_addToSystemPathFlag();
 
 private: