diff --git a/src/main/kotlin/ca/gosyer/common/io/OkioExtensions.kt b/src/main/kotlin/ca/gosyer/common/io/OkioExtensions.kt
index 0a23c11a..dab9a6da 100644
--- a/src/main/kotlin/ca/gosyer/common/io/OkioExtensions.kt
+++ b/src/main/kotlin/ca/gosyer/common/io/OkioExtensions.kt
@@ -11,12 +11,12 @@ import okio.BufferedSink
 import okio.Source
 import okio.buffer
 import okio.sink
-import java.io.File
+import java.nio.file.Path
 
-suspend fun Source.saveTo(file: File) {
+suspend fun Source.saveTo(path: Path) {
     withIOContext {
         use { source ->
-            file.sink().buffer().use { it.writeAll(source) }
+            path.sink().buffer().use { it.writeAll(source) }
         }
     }
 }
diff --git a/src/main/kotlin/ca/gosyer/core/logging/LoggingSetup.kt b/src/main/kotlin/ca/gosyer/core/logging/LoggingSetup.kt
index c5fcf560..739ee203 100644
--- a/src/main/kotlin/ca/gosyer/core/logging/LoggingSetup.kt
+++ b/src/main/kotlin/ca/gosyer/core/logging/LoggingSetup.kt
@@ -16,7 +16,8 @@ import org.apache.logging.log4j.core.appender.ConsoleAppender
 import org.apache.logging.log4j.core.config.builder.api.ComponentBuilder
 import org.apache.logging.log4j.core.config.builder.api.ConfigurationBuilderFactory
 import org.slf4j.bridge.SLF4JBridgeHandler
-import java.io.File
+import java.nio.file.Path
+import kotlin.io.path.absolutePathString
 import java.util.logging.LogManager as JLogManager
 
 const val consolePattern =
@@ -37,7 +38,7 @@ const val filePattern =
         "{LOG_EXCEPTION_CONVERSION_WORD:-%xEx}"
 
 @Suppress("UPPER_BOUND_VIOLATED_WARNING")
-fun initializeLogger(loggingLocation: File) {
+fun initializeLogger(loggingLocation: Path) {
     val ctx = LogManager.getContext(false) as LoggerContext
     val builder = ConfigurationBuilderFactory.newConfigurationBuilder()
         .apply {
@@ -59,11 +60,11 @@ fun initializeLogger(loggingLocation: File) {
                 newAppender("Rolling", "RollingFile")
                     .addAttribute(
                         "fileName",
-                        loggingLocation.absolutePath.trimEnd { it == '/' || it == '\\' } + "/rolling.log"
+                        loggingLocation.absolutePathString().trimEnd { it == '/' || it == '\\' } + "/rolling.log"
                     )
                     .addAttribute(
                         "filePattern",
-                        loggingLocation.absolutePath.trimEnd { it == '/' || it == '\\' } + "/archive/rolling-%d{yyyy-MM-dd-}.log.gz"
+                        loggingLocation.absolutePathString().trimEnd { it == '/' || it == '\\' } + "/archive/rolling-%d{yyyy-MM-dd-}.log.gz"
                     )
                     .add(
                         newLayout("PatternLayout")
diff --git a/src/main/kotlin/ca/gosyer/data/server/ServerService.kt b/src/main/kotlin/ca/gosyer/data/server/ServerService.kt
index e17c1ca1..96dbedb7 100644
--- a/src/main/kotlin/ca/gosyer/data/server/ServerService.kt
+++ b/src/main/kotlin/ca/gosyer/data/server/ServerService.kt
@@ -21,13 +21,22 @@ import kotlinx.coroutines.flow.mapLatest
 import kotlinx.coroutines.flow.merge
 import kotlinx.coroutines.launch
 import mu.KotlinLogging
-import java.io.File
+import java.io.File.pathSeparatorChar
 import java.io.IOException
 import java.io.Reader
+import java.nio.file.Path
 import java.util.jar.Attributes
 import java.util.jar.JarInputStream
 import javax.inject.Inject
 import kotlin.concurrent.thread
+import kotlin.io.path.Path
+import kotlin.io.path.absolutePathString
+import kotlin.io.path.createDirectories
+import kotlin.io.path.exists
+import kotlin.io.path.inputStream
+import kotlin.io.path.isExecutable
+import kotlin.io.path.name
+import kotlin.io.path.outputStream
 
 @OptIn(DelicateCoroutinesApi::class)
 class ServerService @Inject constructor(
@@ -55,7 +64,7 @@ class ServerService @Inject constructor(
     }
 
     @Throws(IOException::class)
-    private fun copyJar(jarFile: File) {
+    private fun copyJar(jarFile: Path) {
         javaClass.getResourceAsStream("/Tachidesk.jar")?.buffered()?.use { input ->
             jarFile.outputStream().use { output ->
                 input.copyTo(output)
@@ -63,30 +72,30 @@ class ServerService @Inject constructor(
         }
     }
 
-    private fun getJavaFromPath(javaPath: File): String? {
-        val javaExeFile = File(javaPath, "java.exe")
-        val javaUnixFile = File(javaPath, "java")
+    private fun getJavaFromPath(javaPath: Path): String? {
+        val javaExeFile = javaPath.resolve("java.exe")
+        val javaUnixFile = javaPath.resolve("java")
         return when {
-            javaExeFile.exists() && javaExeFile.canExecute() -> javaExeFile.absolutePath
-            javaUnixFile.exists() && javaUnixFile.canExecute() -> javaUnixFile.absolutePath
+            javaExeFile.exists() && javaExeFile.isExecutable() -> javaExeFile.absolutePathString()
+            javaUnixFile.exists() && javaUnixFile.isExecutable() -> javaUnixFile.absolutePathString()
             else -> null
         }
     }
 
     private fun getRuntimeJava(): String? {
-        return System.getProperty("java.home")?.let { getJavaFromPath(File(it, "bin")) }
+        return System.getProperty("java.home")?.let { getJavaFromPath(Path(it).resolve("bin")) }
     }
 
     private fun getPossibleJava(): String? {
-        return System.getProperty("java.library.path")?.split(File.pathSeparatorChar)
+        return System.getProperty("java.library.path")?.split(pathSeparatorChar)
             .orEmpty()
             .asSequence()
             .mapNotNull {
-                val file = File(it)
-                if (file.absolutePath.contains("java") || file.absolutePath.contains("jdk")) {
+                val file = Path(it)
+                if (file.absolutePathString().contains("java") || file.absolutePathString().contains("jdk")) {
                     if (file.name.equals("bin", true)) {
                         file
-                    } else File(file, "bin")
+                    } else file.resolve("bin")
                 } else null
             }
             .mapNotNull { getJavaFromPath(it) }
@@ -117,7 +126,7 @@ class ServerService @Inject constructor(
                 }
             }
             GlobalScope.launch(handler) {
-                val jarFile = File(userDataDir.also { it.mkdirs() }, "Tachidesk.jar")
+                val jarFile = userDataDir.also { it.createDirectories() }.resolve("Tachidesk.jar")
                 if (!jarFile.exists()) {
                     info { "Copying server to resources" }
                     withIOContext { copyJar(jarFile) }
@@ -147,7 +156,7 @@ class ServerService @Inject constructor(
 
                 withIOContext {
                     val reader: Reader
-                    process = ProcessBuilder(javaPath, *properties, "-jar", jarFile.absolutePath)
+                    process = ProcessBuilder(javaPath, *properties, "-jar", jarFile.absolutePathString())
                         .redirectErrorStream(true)
                         .start()
                         .also {
diff --git a/src/main/kotlin/ca/gosyer/data/server/interactions/BackupInteractionHandler.kt b/src/main/kotlin/ca/gosyer/data/server/interactions/BackupInteractionHandler.kt
index 82285983..6b3a88e6 100644
--- a/src/main/kotlin/ca/gosyer/data/server/interactions/BackupInteractionHandler.kt
+++ b/src/main/kotlin/ca/gosyer/data/server/interactions/BackupInteractionHandler.kt
@@ -21,15 +21,16 @@ import io.ktor.client.statement.HttpResponse
 import io.ktor.http.ContentType
 import io.ktor.http.Headers
 import io.ktor.http.HttpHeaders
-import java.io.File
+import java.nio.file.Path
 import javax.inject.Inject
+import kotlin.io.path.readBytes
 
 class BackupInteractionHandler @Inject constructor(
     client: Http,
     serverPreferences: ServerPreferences
 ) : BaseInteractionHandler(client, serverPreferences) {
 
-    suspend fun importBackupFile(file: File, block: HttpRequestBuilder.() -> Unit = {}) = withIOContext {
+    suspend fun importBackupFile(file: Path, block: HttpRequestBuilder.() -> Unit = {}) = withIOContext {
         client.submitFormWithBinaryData<HttpResponse>(
             serverUrl + backupFileImportRequest(),
             formData = formData {
@@ -45,7 +46,7 @@ class BackupInteractionHandler @Inject constructor(
         )
     }
 
-    suspend fun validateBackupFile(file: File, block: HttpRequestBuilder.() -> Unit = {}) = withIOContext {
+    suspend fun validateBackupFile(file: Path, block: HttpRequestBuilder.() -> Unit = {}) = withIOContext {
         client.submitFormWithBinaryData<BackupValidationResult>(
             serverUrl + validateBackupFileRequest(),
             formData = formData {
diff --git a/src/main/kotlin/ca/gosyer/ui/main/main.kt b/src/main/kotlin/ca/gosyer/ui/main/main.kt
index f02950ba..d5e59623 100644
--- a/src/main/kotlin/ca/gosyer/ui/main/main.kt
+++ b/src/main/kotlin/ca/gosyer/ui/main/main.kt
@@ -52,13 +52,12 @@ import org.jetbrains.skiko.currentSystemTheme
 import toothpick.configuration.Configuration
 import toothpick.ktp.KTP
 import toothpick.ktp.extension.getInstance
-import java.io.File
 import java.util.Locale
 import kotlin.system.exitProcess
 
 @OptIn(DelicateCoroutinesApi::class)
 suspend fun main() {
-    initializeLogger(File(userDataDir, "logging"))
+    initializeLogger(userDataDir.resolve(userDataDir, "logging"))
 
     if (BuildConfig.DEBUG) {
         System.setProperty("kotlinx.coroutines.debug", "on")
diff --git a/src/main/kotlin/ca/gosyer/ui/settings/SettingsBackupScreen.kt b/src/main/kotlin/ca/gosyer/ui/settings/SettingsBackupScreen.kt
index 6f159526..9b393736 100644
--- a/src/main/kotlin/ca/gosyer/ui/settings/SettingsBackupScreen.kt
+++ b/src/main/kotlin/ca/gosyer/ui/settings/SettingsBackupScreen.kt
@@ -47,8 +47,11 @@ import kotlinx.coroutines.flow.asSharedFlow
 import kotlinx.coroutines.flow.asStateFlow
 import kotlinx.coroutines.flow.collect
 import kotlinx.coroutines.launch
-import java.io.File
+import java.nio.file.Path
 import javax.inject.Inject
+import kotlin.io.path.absolutePathString
+import kotlin.io.path.notExists
+import kotlin.io.path.outputStream
 
 class SettingsBackupViewModel @Inject constructor(
     private val backupHandler: BackupInteractionHandler
@@ -59,7 +62,7 @@ class SettingsBackupViewModel @Inject constructor(
     val restoringProgress = _restoringProgress.asStateFlow()
     private val _restoreStatus = MutableStateFlow<Status>(Status.Nothing)
     internal val restoreStatus = _restoreStatus.asStateFlow()
-    private val _missingSourceFlow = MutableSharedFlow<Pair<File, List<String>>>()
+    private val _missingSourceFlow = MutableSharedFlow<Pair<Path, List<String>>>()
     val missingSourceFlow = _missingSourceFlow.asSharedFlow()
 
     private val _creating = MutableStateFlow(false)
@@ -68,13 +71,13 @@ class SettingsBackupViewModel @Inject constructor(
     val creatingProgress = _creatingProgress.asStateFlow()
     private val _creatingStatus = MutableStateFlow<Status>(Status.Nothing)
     internal val creatingStatus = _creatingStatus.asStateFlow()
-    private val _createFlow = MutableSharedFlow<Pair<String, (File) -> Unit>>()
+    private val _createFlow = MutableSharedFlow<Pair<String, (Path) -> Unit>>()
     val createFlow = _createFlow.asSharedFlow()
 
-    fun restoreFile(file: File?) {
+    fun restoreFile(file: Path?) {
         scope.launch {
-            if (file == null || !file.exists()) {
-                info { "Invalid file ${file?.absolutePath}" }
+            if (file == null || file.notExists()) {
+                info { "Invalid file ${file?.absolutePathString()}" }
                 _restoreStatus.value = Status.Error
                 _restoring.value = false
             } else {
@@ -94,7 +97,7 @@ class SettingsBackupViewModel @Inject constructor(
         }
     }
 
-    fun restoreBackup(file: File) {
+    fun restoreBackup(file: Path) {
         scope.launch {
             _restoreStatus.value = Status.Nothing
             _restoringProgress.value = null
@@ -189,7 +192,7 @@ fun SettingsBackupScreen(menuController: MenuController) {
         launch {
             vm.createFlow.collect { (filename, function) ->
                 fileSaver(filename, "proto.gz") {
-                    function(it.selectedFile)
+                    function(it.selectedFile.toPath())
                 }
             }
         }
@@ -207,7 +210,7 @@ fun SettingsBackupScreen(menuController: MenuController) {
                     restoreStatus
                 ) {
                     filePicker("gz") {
-                        vm.restoreFile(it.selectedFile)
+                        vm.restoreFile(it.selectedFile.toPath())
                     }
                 }
                 PreferenceFile(
diff --git a/src/main/kotlin/ca/gosyer/util/compose/Image.kt b/src/main/kotlin/ca/gosyer/util/compose/Image.kt
index 019ffc75..39493763 100644
--- a/src/main/kotlin/ca/gosyer/util/compose/Image.kt
+++ b/src/main/kotlin/ca/gosyer/util/compose/Image.kt
@@ -13,11 +13,12 @@ import io.ktor.client.request.HttpRequestBuilder
 import io.ktor.client.request.get
 import io.ktor.utils.io.ByteReadChannel
 import io.ktor.utils.io.jvm.javaio.copyTo
-import org.jetbrains.skija.Image
+import org.jetbrains.skia.Image
 import java.io.ByteArrayOutputStream
-import java.io.File
+import java.nio.file.Path
+import kotlin.io.path.readBytes
 
-fun imageFromFile(file: File): ImageBitmap {
+fun imageFromFile(file: Path): ImageBitmap {
     return Image.makeFromEncoded(file.readBytes()).asImageBitmap()
 }
 
diff --git a/src/main/kotlin/ca/gosyer/util/system/File.kt b/src/main/kotlin/ca/gosyer/util/system/File.kt
index c81eaf78..b9921001 100644
--- a/src/main/kotlin/ca/gosyer/util/system/File.kt
+++ b/src/main/kotlin/ca/gosyer/util/system/File.kt
@@ -12,9 +12,12 @@ import kotlinx.coroutines.DelicateCoroutinesApi
 import mu.KotlinLogging
 import net.harawata.appdirs.AppDirs
 import net.harawata.appdirs.AppDirsFactory
-import java.io.File
+import java.nio.file.Path
 import javax.swing.JFileChooser
 import javax.swing.filechooser.FileNameExtensionFilter
+import kotlin.io.path.Path
+import kotlin.io.path.createDirectories
+import kotlin.io.path.exists
 
 private val logger = KotlinLogging.logger {}
 
@@ -22,10 +25,10 @@ val appDirs: AppDirs by lazy {
     AppDirsFactory.getInstance()
 }
 
-val userDataDir: File by lazy {
-    File(appDirs.getUserDataDir(BuildConfig.NAME, null, null)).also {
+val userDataDir: Path by lazy {
+    Path(appDirs.getUserDataDir(BuildConfig.NAME, null, null)).also {
         if (!it.exists()) {
-            logger.info("Attempted to create app data dir, result: {}", it.mkdirs())
+            logger.info("Attempted to create app data dir, result: {}", it.createDirectories())
         }
     }
 }
@@ -82,7 +85,7 @@ private fun fileChooser(
                 fileFilter = FileNameExtensionFilter("${extensions.joinToString()} files", *extensions)
             }
             if (saving) {
-                selectedFile = File(defaultFileName)
+                selectedFile = Path(defaultFileName).toFile()
             }
         }
         .apply(builder)