diff --git a/test_runner/src/main/kotlin/ftl/args/AndroidArgs.kt b/test_runner/src/main/kotlin/ftl/args/AndroidArgs.kt
index ba267f7228..504b5b0eb2 100644
--- a/test_runner/src/main/kotlin/ftl/args/AndroidArgs.kt
+++ b/test_runner/src/main/kotlin/ftl/args/AndroidArgs.kt
@@ -10,6 +10,7 @@ import ftl.android.UnsupportedVersionId
 import ftl.args.ArgsHelper.assertFileExists
 import ftl.args.ArgsHelper.assertGcsFileExists
 import ftl.args.ArgsHelper.calculateShards
+import ftl.args.ArgsHelper.evaluateFilePath
 import ftl.args.ArgsHelper.getGcsBucket
 import ftl.args.ArgsHelper.mergeYmlMaps
 import ftl.args.ArgsHelper.yamlMapper
@@ -45,8 +46,8 @@ class AndroidArgs(
     override val resultsHistoryName = gcloud.resultsHistoryName
 
     private val androidGcloud = androidGcloudYml.gcloud
-    val appApk = androidGcloud.app
-    val testApk = androidGcloud.test
+    var appApk = androidGcloud.app
+    var testApk = androidGcloud.test
     val autoGoogleLogin = androidGcloud.autoGoogleLogin
     val useOrchestrator = androidGcloud.useOrchestrator
     val environmentVariables = androidGcloud.environmentVariables
@@ -85,12 +86,14 @@ class AndroidArgs(
         if (appApk.startsWith(FtlConstants.GCS_PREFIX)) {
             assertGcsFileExists(appApk)
         } else {
+            appApk = evaluateFilePath(appApk, "appApk")
             assertFileExists(appApk, "appApk")
         }
 
         if (testApk.startsWith(FtlConstants.GCS_PREFIX)) {
             assertGcsFileExists(testApk)
         } else {
+            testApk = evaluateFilePath(testApk, "testApk")
             assertFileExists(testApk, "testApk")
         }
 
diff --git a/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt b/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
index 66523352ed..612067ba23 100644
--- a/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
+++ b/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
@@ -20,9 +20,18 @@ import ftl.config.FtlConstants.defaultCredentialPath
 import ftl.gc.GcStorage
 import ftl.util.Utils
 import java.io.File
+import java.io.IOException
 import java.math.RoundingMode
 import java.net.URI
+import java.nio.file.FileVisitResult
 import java.nio.file.Files
+import java.nio.file.FileSystems
+import java.nio.file.SimpleFileVisitor
+import java.nio.file.attribute.BasicFileAttributes
+import java.nio.file.Path
+import java.nio.file.Paths
+import java.util.HashSet
+import java.util.regex.Pattern
 
 object ArgsHelper {
 
@@ -45,6 +54,19 @@ object ArgsHelper {
         }
     }
 
+    fun evaluateFilePath(fileRegEx: String, name: String): String {
+        var file = fileRegEx.trim().replaceFirst("~", System.getProperty("user.home"))
+        file = substituteEnvVars(file)
+        val searchDirectoryPath = getSearchDirectoryPath(file)
+        val filePaths = getAbsoluteFilePaths(searchDirectoryPath, file)
+        if (filePaths.size > 1) {
+            Utils.fatalError("$name multiple files found with expression: `$fileRegEx`: $filePaths")
+        } else if (filePaths.isEmpty()) {
+            Utils.fatalError("'$fileRegEx' $name doesn't exist")
+        }
+        return filePaths[0].toAbsolutePath().toString()
+    }
+
     fun assertGcsFileExists(uri: String) {
         if (!uri.startsWith(GCS_PREFIX)) {
             throw IllegalArgumentException("must start with $GCS_PREFIX uri: $uri")
@@ -150,4 +172,53 @@ object ArgsHelper {
         // Allow users control over projectId by checking using Google's logic first before falling back to JSON.
         return ServiceOptions.getDefaultProjectId() ?: serviceAccountProjectId()
     }
+
+    private fun getSearchDirectoryPath(path: String): String {
+        var searchDirectoryPath = String()
+        val pattern = "([^*]*/)"
+        val matcher = Pattern.compile(pattern).matcher(path)
+        if (matcher.find()) {
+            searchDirectoryPath = matcher.group(1)
+        }
+        return searchDirectoryPath
+    }
+
+    private fun substituteEnvVars(text: String): String {
+        val sb = StringBuffer()
+        // https://stackoverflow.com/a/2821201/2450315
+        val pattern = "\\$([a-zA-Z_]{1,}[a-zA-Z0-9_]{0,})"
+        val matcher = Pattern.compile(pattern).matcher(text)
+        while (matcher.find()) {
+            val varname = matcher.group(1)
+            val envValue: String = System.getenv(varname) ?: ""
+            matcher.appendReplacement(sb, envValue)
+        }
+        matcher.appendTail(sb)
+        return sb.toString()
+    }
+
+    private fun getAbsoluteFilePaths(searchDir: String, globPath: String): List<Path> {
+        val maxDepth = if (globPath.contains("/*")) Integer.MAX_VALUE else 1
+        val glob = "glob:$globPath"
+        val paths = ArrayList<Path>()
+        val pathMatcher = FileSystems.getDefault().getPathMatcher(glob)
+
+        Files.walkFileTree(Paths.get(searchDir), HashSet(), maxDepth, object : SimpleFileVisitor<Path>() {
+
+            @Throws(IOException::class)
+            override fun visitFile(path: Path, attrs: BasicFileAttributes): FileVisitResult {
+                if (pathMatcher.matches(path)) {
+                    paths.add(path)
+                }
+                return FileVisitResult.CONTINUE
+            }
+
+            @Throws(IOException::class)
+            override fun visitFileFailed(file: Path, exc: IOException?): FileVisitResult {
+                Utils.fatalError("'$file' doesn't exist")
+                return FileVisitResult.CONTINUE
+            }
+        })
+        return paths
+    }
 }
diff --git a/test_runner/src/main/kotlin/ftl/args/IosArgs.kt b/test_runner/src/main/kotlin/ftl/args/IosArgs.kt
index cb380c76b7..b8458b08e5 100644
--- a/test_runner/src/main/kotlin/ftl/args/IosArgs.kt
+++ b/test_runner/src/main/kotlin/ftl/args/IosArgs.kt
@@ -2,6 +2,7 @@ package ftl.args
 
 import ftl.args.ArgsHelper.assertFileExists
 import ftl.args.ArgsHelper.assertGcsFileExists
+import ftl.args.ArgsHelper.evaluateFilePath
 import ftl.args.ArgsHelper.mergeYmlMaps
 import ftl.args.ArgsHelper.validateTestMethods
 import ftl.args.ArgsHelper.yamlMapper
@@ -36,8 +37,8 @@ class IosArgs(
     override val resultsHistoryName = gcloud.resultsHistoryName
 
     private val iosGcloud = iosGcloudYml.gcloud
-    val xctestrunZip = iosGcloud.test
-    val xctestrunFile = iosGcloud.xctestrunFile
+    var xctestrunZip = iosGcloud.test
+    var xctestrunFile = iosGcloud.xctestrunFile
     val xcodeVersion = iosGcloud.xcodeVersion
     val devices = iosGcloud.device
 
@@ -70,8 +71,10 @@ class IosArgs(
         if (xctestrunZip.startsWith(FtlConstants.GCS_PREFIX)) {
             assertGcsFileExists(xctestrunZip)
         } else {
+            xctestrunZip = evaluateFilePath(xctestrunZip, "xctestrunZip")
             assertFileExists(xctestrunZip, "xctestrunZip")
         }
+        xctestrunFile = evaluateFilePath(xctestrunFile, "xctestrunFile")
         assertFileExists(xctestrunFile, "xctestrunFile")
 
         devices.forEach { device -> assertDeviceSupported(device) }
diff --git a/test_runner/src/test/kotlin/ftl/args/AndroidArgsFileTest.kt b/test_runner/src/test/kotlin/ftl/args/AndroidArgsFileTest.kt
index 065e5cec92..e56158b6e4 100644
--- a/test_runner/src/test/kotlin/ftl/args/AndroidArgsFileTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/AndroidArgsFileTest.kt
@@ -17,6 +17,7 @@ import org.junit.contrib.java.lang.system.SystemErrRule
 import org.junit.contrib.java.lang.system.SystemOutRule
 import org.junit.rules.ExpectedException
 import org.junit.runner.RunWith
+import java.io.File
 
 @RunWith(FlankTestRunner::class)
 class AndroidArgsFileTest {
@@ -42,6 +43,8 @@ class AndroidArgsFileTest {
     private val testName = "class com.example.app.ExampleUiTest#testPasses"
     private val directoryToPull = "/sdcard/screenshots"
 
+    private val appApkAbsolutePath = File(appApkLocal).absolutePath
+    private val testApkAbsolutePath = File(testApkLocal).absolutePath
     // NOTE: Change working dir to '%MODULE_WORKING_DIR%' in IntelliJ to match gradle for this test to pass.
     @Test
     fun localConfigLoadsSuccessfully() {
@@ -58,10 +61,10 @@ class AndroidArgsFileTest {
     private fun checkConfig(args: AndroidArgs, local: Boolean) {
 
         with(args) {
-            if (local) assert(getString(testApk), testApkLocal)
+            if (local) assert(getString(testApk), getString(testApkAbsolutePath))
             else assert(testApk, testApkGcs)
 
-            if (local) assert(getString(appApk), appApkLocal)
+            if (local) assert(getString(appApk), getString(appApkAbsolutePath))
             else assert(appApk, appApkGcs)
 
             assert(autoGoogleLogin, true)
diff --git a/test_runner/src/test/kotlin/ftl/args/AndroidArgsTest.kt b/test_runner/src/test/kotlin/ftl/args/AndroidArgsTest.kt
index 9f7b68b645..6142513437 100644
--- a/test_runner/src/test/kotlin/ftl/args/AndroidArgsTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/AndroidArgsTest.kt
@@ -8,6 +8,7 @@ import org.junit.Rule
 import org.junit.Test
 import org.junit.rules.ExpectedException
 import org.junit.runner.RunWith
+import java.io.File
 
 @RunWith(FlankTestRunner::class)
 class AndroidArgsTest {
@@ -15,6 +16,8 @@ class AndroidArgsTest {
     private val appApk = "../test_app/apks/app-debug.apk"
     private val testApk = "../test_app/apks/app-debug-androidTest.apk"
     private val testErrorApk = "../test_app/apks/error-androidTest.apk"
+    private val appApkAbsolutePath = File(appApk).absolutePath
+    private val testApkAbsolutePath = File(testApk).absolutePath
 
     private val androidNonDefault = """
         gcloud:
@@ -123,8 +126,8 @@ class AndroidArgsTest {
             assert(resultsHistoryName ?: "", "android-history")
 
             // AndroidGcloudYml
-            assert(appApk, appApk)
-            assert(testApk, testApk)
+            assert(appApk, appApkAbsolutePath)
+            assert(testApk, testApkAbsolutePath)
             assert(autoGoogleLogin, false)
             assert(useOrchestrator, false)
             assert(environmentVariables, linkedMapOf("clearPackageData" to "true", "randomEnvVar" to "false"))
@@ -170,8 +173,8 @@ AndroidArgs
       project: projectFoo
       results-history-name: android-history
       # Android gcloud
-      app: ../test_app/apks/app-debug.apk
-      test: ../test_app/apks/app-debug-androidTest.apk
+      app: $appApkAbsolutePath
+      test: $testApkAbsolutePath
       auto-google-login: false
       use-orchestrator: false
       environment-variables:
@@ -223,8 +226,8 @@ AndroidArgs
             assert(projectId, "mockProjectId")
 
             // AndroidGcloudYml
-            assert(appApk, appApk)
-            assert(testApk, testApk)
+            assert(appApk, appApkAbsolutePath)
+            assert(testApk, testApkAbsolutePath)
             assert(autoGoogleLogin, true)
             assert(useOrchestrator, true)
             assert(environmentVariables, emptyMap<String, String>())
@@ -272,7 +275,7 @@ AndroidArgs
       """
         )
 
-        assertThat(androidArgs.appApk).isEqualTo(appApk)
-        assertThat(androidArgs.testApk).isEqualTo(testApk)
+        assertThat(androidArgs.appApk).isEqualTo(appApkAbsolutePath)
+        assertThat(androidArgs.testApk).isEqualTo(testApkAbsolutePath)
     }
 }
diff --git a/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt b/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
index 7e5a5d8361..3e98363f4d 100644
--- a/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
@@ -15,6 +15,9 @@ import org.junit.Test
 import org.junit.contrib.java.lang.system.SystemErrRule
 import org.junit.rules.ExpectedException
 import org.junit.runner.RunWith
+import java.io.File
+import org.junit.contrib.java.lang.system.EnvironmentVariables
+import java.lang.RuntimeException
 
 @RunWith(FlankTestRunner::class)
 class ArgsHelperTest {
@@ -27,6 +30,9 @@ class ArgsHelperTest {
     @JvmField
     val systemErrRule = SystemErrRule().muteForSuccessfulTests()!!
 
+    @get:Rule
+    val environmentVariables = EnvironmentVariables()
+
     @Test
     fun mergeYmlMaps_succeeds() {
         val merged = mergeYmlMaps(GcloudYml, IosGcloudYml)
@@ -161,4 +167,43 @@ class ArgsHelperTest {
         assertThat(ArgsHelper.getDefaultProjectId())
             .isEqualTo("mockProjectId")
     }
+
+    @Test
+    fun evaluateBlobInFilePath() {
+        val testApkRelativePath = "../test_app/apks/app-debug-androidTest.apk"
+        val testApkBlobPath = "../test_app/**/app-debug-*.apk"
+
+        assertThat(File(testApkRelativePath).absolutePath)
+            .isEqualTo(ArgsHelper.evaluateFilePath(testApkBlobPath, "test"))
+    }
+
+    @Test
+    fun evaluateTildeInFilePath() {
+        val testApkPath = "~/flank_test_app/random.xctestrun"
+        val file = File(testApkPath.replaceFirst("~", System.getProperty("user.home")))
+        file.getParentFile().mkdirs()
+        file.createNewFile()
+
+        assertThat(file.absolutePath)
+            .isEqualTo(ArgsHelper.evaluateFilePath(testApkPath, "xctestrun-file"))
+    }
+
+    @Test
+    fun evaluateEnvVarInFilePath() {
+        environmentVariables.set("TEST_APK_DIR", "test_app/apks")
+        val testApkPath = "../\$TEST_APK_DIR/app-debug-androidTest.apk"
+        val expectedPath = File("../test_app/apks/app-debug-androidTest.apk").absolutePath
+        val file = File(testApkPath.replaceFirst("~", System.getProperty("user.home")))
+        file.getParentFile().mkdirs()
+        file.createNewFile()
+
+        assertThat(expectedPath)
+            .isEqualTo(ArgsHelper.evaluateFilePath(testApkPath, "test"))
+    }
+
+    @Test(expected = RuntimeException::class)
+    fun evaluateInvalidFilePath() {
+        val testApkPath = "~/flank_test_app/invalid_path/app-debug-*.xctestrun"
+        ArgsHelper.evaluateFilePath(testApkPath, "test")
+    }
 }
diff --git a/test_runner/src/test/kotlin/ftl/args/IosArgsTest.kt b/test_runner/src/test/kotlin/ftl/args/IosArgsTest.kt
index 26a7f6e52f..0e1c716640 100644
--- a/test_runner/src/test/kotlin/ftl/args/IosArgsTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/IosArgsTest.kt
@@ -14,6 +14,7 @@ import org.junit.Test
 import org.junit.contrib.java.lang.system.SystemErrRule
 import org.junit.rules.ExpectedException
 import org.junit.runner.RunWith
+import java.io.File
 
 @RunWith(FlankTestRunner::class)
 class IosArgsTest {
@@ -21,6 +22,8 @@ class IosArgsTest {
     private val testPath = "./src/test/kotlin/ftl/fixtures/tmp/EarlGreyExample.zip"
     private val xctestrunFile =
         "./src/test/kotlin/ftl/fixtures/tmp/EarlGreyExampleSwiftTests_iphoneos12.1-arm64e.xctestrun"
+    val xctestrunFileAbsolutePath = File(xctestrunFile).absolutePath
+    val testAbsolutePath = File(testPath).absolutePath
     private val iosNonDefault = """
         gcloud:
           results-bucket: mockBucket
@@ -101,8 +104,8 @@ class IosArgsTest {
             assert(resultsHistoryName ?: "", "ios-history")
 
             // IosGcloudYml
-            assert(xctestrunZip, testPath)
-            assert(xctestrunFile, xctestrunFile)
+            assert(xctestrunZip, testAbsolutePath)
+            assert(xctestrunFile, xctestrunFileAbsolutePath)
             val device = Device("iphone8", "11.2", "c", "d")
             assert(xcodeVersion ?: "", "9.2")
             assert(devices, listOf(device, device))
@@ -131,8 +134,8 @@ IosArgs
       project: projectFoo
       results-history-name: ios-history
       # iOS gcloud
-      test: $testPath
-      xctestrun-file: $xctestrunFile
+      test: $testAbsolutePath
+      xctestrun-file: $xctestrunFileAbsolutePath
       xcode-version: 9.2
       device:
         - model: iphone8
@@ -177,8 +180,8 @@ IosArgs
             assert(projectId, "mockProjectId")
 
             // IosGcloudYml
-            assert(xctestrunZip, testPath)
-            assert(xctestrunFile, xctestrunFile)
+            assert(xctestrunZip, testAbsolutePath)
+            assert(xctestrunFile, xctestrunFileAbsolutePath)
             assert(devices, listOf(Device("iphone8", "11.2")))
 
             // FlankYml
@@ -224,8 +227,8 @@ IosArgs
         )
 
         with(iosArgs) {
-            assertThat(xctestrunZip).isEqualTo(testPath)
-            assertThat(xctestrunFile).isEqualTo(xctestrunFile)
+            assertThat(xctestrunZip).isEqualTo(testAbsolutePath)
+            assertThat(xctestrunFile).isEqualTo(xctestrunFileAbsolutePath)
         }
     }
 }