sffej
diff --git a/‎src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt
Lines changed: 3 additions & 2 deletions b/‎src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt
Lines changed: 3 additions & 2 deletions
diff --git a/‎src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt
Lines changed: 22 additions & 5 deletions b/‎src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt
Lines changed: 22 additions & 5 deletions
@@ -3,6 +3,7 @@ package com.coder.gateway.settings
 import com.coder.gateway.services.CoderSettingsState
 import com.coder.gateway.util.Arch
 import com.coder.gateway.util.OS
+import com.coder.gateway.util.expand
 import com.coder.gateway.util.getArch
 import com.coder.gateway.util.getOS
 import com.coder.gateway.util.safeHost
@@ -39,7 +40,7 @@ open class CoderSettings(
      */
     fun dataDir(url: URL): Path {
         val dir = if (state.dataDirectory.isBlank()) dataDir
-        else Path.of(state.dataDirectory).toAbsolutePath()
+        else Path.of(expand(state.dataDirectory)).toAbsolutePath()
         return withHost(dir, url)
     }
 
@@ -66,7 +67,7 @@ open class CoderSettings(
     fun binPath(url: URL, forceDownloadToData: Boolean = false): Path {
         val binaryName = getCoderCLIForOS(getOS(), getArch())
         val dir = if (forceDownloadToData || state.binaryDirectory.isBlank()) dataDir(url)
-        else withHost(Path.of(state.binaryDirectory).toAbsolutePath(), url)
+        else withHost(Path.of(expand(state.binaryDirectory)).toAbsolutePath(), url)
         return dir.resolve(binaryName)
     }
 
 
@@ -1,18 +1,33 @@
-package com.coder.gateway.services
+package com.coder.gateway.settings
 
+import com.coder.gateway.services.CoderSettingsState
 import kotlin.test.Test
 import kotlin.test.assertContains
 import kotlin.test.assertEquals
 
-import com.coder.gateway.settings.CoderSettings
-import com.coder.gateway.settings.Environment
 import com.coder.gateway.util.OS
 import com.coder.gateway.util.getOS
 import com.coder.gateway.util.withPath
 import java.net.URL
 import java.nio.file.Path
 
 internal class CoderSettingsTest {
+    @Test
+    fun testExpands() {
+        val state = CoderSettingsState()
+        val settings = CoderSettings(state)
+        val url = URL("http://localhost")
+        val home = Path.of(System.getProperty("user.home"))
+
+        state.binaryDirectory = "~/coder-gateway-test/expand-bin-dir"
+        var expected = home.resolve("coder-gateway-test/expand-bin-dir/localhost")
+        assertEquals(expected.toAbsolutePath(), settings.binPath(url).parent)
+
+        state.dataDirectory = "~/coder-gateway-test/expand-data-dir"
+        expected = home.resolve("coder-gateway-test/expand-data-dir/localhost")
+        assertEquals(expected.toAbsolutePath(), settings.dataDir(url))
+    }
+
     @Test
     fun testDataDir() {
         val state = CoderSettingsState()
@@ -162,15 +177,17 @@ internal class CoderSettingsTest {
     @Test
     fun testSettings() {
         // Make sure the remaining settings are being conveyed.
-        val settings = CoderSettings(CoderSettingsState(
+        val settings = CoderSettings(
+            CoderSettingsState(
             enableDownloads = false,
             enableBinaryDirectoryFallback = true,
             headerCommand = "test header",
             tlsCertPath = "tls cert path",
             tlsKeyPath = "tls key path",
             tlsCAPath = "tls ca path",
             tlsAlternateHostname = "tls alt hostname",
-        ))
+        )
+        )
 
         assertEquals(false, settings.enableDownloads)
         assertEquals(true, settings.enableBinaryDirectoryFallback)