diff --git a/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt b/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
index 6a2aca303d..ed968953a2 100644
--- a/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
+++ b/test_runner/src/main/kotlin/ftl/args/ArgsHelper.kt
@@ -49,7 +49,7 @@ object ArgsHelper {
     }
 
     fun evaluateFilePath(filePath: String): String {
-        var file = filePath.trim().replaceFirst("~", System.getProperty("user.home"))
+        var file = filePath.trim().replaceFirst(Regex("^~"), System.getProperty("user.home"))
         file = substituteEnvVars(file)
         // avoid File(..).canonicalPath since that will resolve symlinks
         file = Paths.get(file).toAbsolutePath().normalize().toString()
@@ -180,7 +180,10 @@ object ArgsHelper {
         val matcher = envRegex.matcher(text)
         while (matcher.find()) {
             val envName = matcher.group(1)
-            val envValue = System.getenv(envName) ?: ""
+            val envValue = System.getenv(envName)
+            if (envValue == null) {
+                println("WARNING: $envName not found")
+            }
             matcher.appendReplacement(buffer, envValue)
         }
         matcher.appendTail(buffer)
diff --git a/test_runner/src/test/kotlin/ftl/args/ArgsHelperFilePathTest.kt b/test_runner/src/test/kotlin/ftl/args/ArgsHelperFilePathTest.kt
index 577e02d553..7e45d7fef4 100644
--- a/test_runner/src/test/kotlin/ftl/args/ArgsHelperFilePathTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/ArgsHelperFilePathTest.kt
@@ -59,9 +59,73 @@ class ArgsHelperFilePathTest {
         Truth.assertThat(actual).isEqualTo(expected)
     }
 
+    @Test
+    fun evaluateRelativeFilePath() {
+        val expected = makeTmpFile("/tmp/app-debug.apk")
+        val testApkPath = "~/../../../../../../../../../tmp/app-debug.apk"
+        val actual = ArgsHelper.evaluateFilePath(testApkPath)
+
+        Truth.assertThat(actual).isEqualTo(expected)
+    }
+
+    @Test
+    fun evaluateRelativeAndWildCardsInFilePath() {
+        makeTmpFile("/tmp/tmp1/tmp2/tmp3/tmp4/tmp5/tmp6/tmp7/tmp8/tmp9/app-debug.apk")
+        val expected = makeTmpFile("/tmp/tmp1/tmp2/tmp3/tmp4/tmp5/tmp6/tmp7/tmp8/tmp9/tmp10/app-debug.apk")
+        val inputPath = "~/../../../../../../../../../tmp/tmp1/**/tmp4/**/tmp7/*/tmp9/*/app*debug.apk"
+        val actual = ArgsHelper.evaluateFilePath(inputPath)
+
+        Truth.assertThat(actual).isEqualTo(expected)
+    }
+
+    @Test
+    fun evaluateWildCardsInFilePath() {
+        val expected = makeTmpFile("/tmp/tmp1/tmp2/tmp3/tmp4/tmp5/tmp6/tmp7/tmp8/tmp9/app-debug.apk")
+        makeTmpFile("/tmp/tmp1/tmp2/tmp3/tmp4/tmp5/tmp6/tmp7/tmp8/tmp9/tmp10/app-debug.apk")
+        val inputPath = "/tmp/**/tmp4/**/tmp8/*/app*debug.apk"
+        val actual = ArgsHelper.evaluateFilePath(inputPath)
+
+        Truth.assertThat(actual).isEqualTo(expected)
+    }
+
+
+    @Test(expected = RuntimeException::class)
+    fun wildCardsInFileNameWithMultipleMatches() {
+        makeTmpFile("/tmp/tmp1/app-debug.apk")
+        makeTmpFile("/tmp/tmp1/app---debug.apk")
+        val inputPath = "/tmp/tmp1/app*debug.apk"
+        ArgsHelper.evaluateFilePath(inputPath)
+    }
+
+
+    @Test(expected = RuntimeException::class)
+    fun wildCardsInFilePathWithMultipleMatches() {
+        makeTmpFile("/tmp/tmp1/tmp2/tmp3/app-debug.apk")
+        makeTmpFile("/tmp/tmp1/tmp2/tmp3/tmp4/app-debug.apk")
+        val inputPath = "~/../../../../../../../../../tmp/**/tmp2/**/app*debug.apk"
+        ArgsHelper.evaluateFilePath(inputPath)
+    }
+
+    @Test
+    fun evaluateMultipleEnvVarsInFilePath() {
+        val expected = makeTmpFile("/tmp/tmp/random.xctestrun")
+        environmentVariables.set("TMP_DIR", "tmp")
+        environmentVariables.set("RANDOM_FILE", "random")
+        val inputPath = "/\$TMP_DIR/\$TMP_DIR/\$RANDOM_FILE.xctestrun"
+        val actual = ArgsHelper.evaluateFilePath(inputPath)
+
+        Truth.assertThat(actual).isEqualTo(expected)
+    }
+
     @Test(expected = java.nio.file.NoSuchFileException::class)
     fun evaluateInvalidFilePath() {
         val testApkPath = "~/flank_test_app/invalid_path/app-debug-*.xctestrun"
         ArgsHelper.evaluateFilePath(testApkPath)
     }
+
+    @Test(expected = java.nio.file.NoSuchFileException::class)
+    fun evaluateInvalidFilePathWithTilde() {
+        val testApkPath = "~/flank_test_app/~/invalid_path/app-debug-*.xctestrun"
+        ArgsHelper.evaluateFilePath(testApkPath)
+    }
 }
diff --git a/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt b/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
index 7f0e5dd6c0..1eb9702c0c 100644
--- a/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
+++ b/test_runner/src/test/kotlin/ftl/args/ArgsHelperTest.kt
@@ -238,7 +238,7 @@ class ArgsHelperTest {
             .isEqualTo(ArgsHelper.evaluateFilePath(testApkPath))
     }
 
-    @Test(expected = RuntimeException::class)
+    @Test(expected = java.nio.file.NoSuchFileException::class)
     fun evaluateInvalidFilePath() {
         val testApkPath = "~/flank_test_app/invalid_path/app-debug-*.xctestrun"
         ArgsHelper.evaluateFilePath(testApkPath)