diff --git a/node-api/src/main/kotlin/net/corda/nodeapi/internal/config/ConfigUtilities.kt b/node-api/src/main/kotlin/net/corda/nodeapi/internal/config/ConfigUtilities.kt
index fd38af42bb..f9f2e0bde9 100644
--- a/node-api/src/main/kotlin/net/corda/nodeapi/internal/config/ConfigUtilities.kt
+++ b/node-api/src/main/kotlin/net/corda/nodeapi/internal/config/ConfigUtilities.kt
@@ -49,8 +49,10 @@ interface ConfigParser<T> {
 const val CUSTOM_NODE_PROPERTIES_ROOT = "custom"
 
 // TODO Move other config parsing to use parseAs and remove this
+// This is to enable constructs like:
+// `val keyStorePassword: String by config`
 operator fun <T : Any> Config.getValue(receiver: Any, metadata: KProperty<*>): T {
-    return getValueInternal(metadata.name, metadata.returnType, UnknownConfigKeysPolicy.IGNORE::handle)
+    return getValueInternal(metadata.name, metadata.returnType, UnknownConfigKeysPolicy.IGNORE::handle, nestedPath = null, baseDirectory = null)
 }
 
 // Problems:
@@ -59,7 +61,8 @@ operator fun <T : Any> Config.getValue(receiver: Any, metadata: KProperty<*>): T
 // - Cannot support a many-to-one relationship between configuration file structures and configuration domain type. This is essential for versioning of the configuration files.
 // - It's complicated and based on reflection, meaning problems with it are typically found at runtime.
 // - It doesn't support validation errors in a structured way. If something goes wrong, it throws exceptions, which doesn't support good usability practices like displaying all the errors at once.
-fun <T : Any> Config.parseAs(clazz: KClass<T>, onUnknownKeys: ((Set<String>, logger: Logger) -> Unit) = UnknownConfigKeysPolicy.FAIL::handle, nestedPath: String? = null): T {
+fun <T : Any> Config.parseAs(clazz: KClass<T>, onUnknownKeys: ((Set<String>, logger: Logger) -> Unit) = UnknownConfigKeysPolicy.FAIL::handle,
+                             nestedPath: String? = null, baseDirectory: Path? = null): T {
     // Use custom parser if provided, instead of treating the object as data class.
     clazz.findAnnotation<CustomConfigParser>()?.let { return uncheckedCast(it.parser.createInstance().parse(this)) }
 
@@ -85,7 +88,7 @@ fun <T : Any> Config.parseAs(clazz: KClass<T>, onUnknownKeys: ((Set<String>, log
         // Get the matching property for this parameter
         val property = clazz.memberProperties.first { it.name == param.name }
         val path = defaultToOldPath(property)
-        getValueInternal<Any>(path, param.type, onUnknownKeys, nestedPath)
+        getValueInternal<Any>(path, param.type, onUnknownKeys, nestedPath, baseDirectory)
     }
     try {
         return constructor.callBy(args)
@@ -114,11 +117,11 @@ fun Config.toProperties(): Properties {
             { it.value.unwrapped().toString() })
 }
 
-private fun <T : Any> Config.getValueInternal(path: String, type: KType, onUnknownKeys: ((Set<String>, logger: Logger) -> Unit), nestedPath: String? = null): T {
-    return uncheckedCast(if (type.arguments.isEmpty()) getSingleValue(path, type, onUnknownKeys, nestedPath) else getCollectionValue(path, type, onUnknownKeys, nestedPath))
+private fun <T : Any> Config.getValueInternal(path: String, type: KType, onUnknownKeys: ((Set<String>, logger: Logger) -> Unit), nestedPath: String?, baseDirectory: Path?): T {
+    return uncheckedCast(if (type.arguments.isEmpty()) getSingleValue(path, type, onUnknownKeys, nestedPath, baseDirectory) else getCollectionValue(path, type, onUnknownKeys, nestedPath, baseDirectory))
 }
 
-private fun Config.getSingleValue(path: String, type: KType, onUnknownKeys: (Set<String>, logger: Logger) -> Unit, nestedPath: String? = null): Any? {
+private fun Config.getSingleValue(path: String, type: KType, onUnknownKeys: (Set<String>, logger: Logger) -> Unit, nestedPath: String?, baseDirectory: Path?): Any? {
     if (type.isMarkedNullable && !hasPath(path)) return null
     val typeClass = type.jvmErasure
     return try {
@@ -132,7 +135,10 @@ private fun Config.getSingleValue(path: String, type: KType, onUnknownKeys: (Set
             Duration::class -> getDuration(path)
             Instant::class -> Instant.parse(getString(path))
             NetworkHostAndPort::class -> NetworkHostAndPort.parse(getString(path))
-            Path::class -> Paths.get(getString(path))
+            Path::class -> {
+                val pathAsString = getString(path)
+                resolvePath(pathAsString, baseDirectory)
+            }
             URL::class -> URL(getString(path))
             UUID::class -> UUID.fromString(getString(path))
             X500Principal::class -> X500Principal(getString(path))
@@ -147,7 +153,7 @@ private fun Config.getSingleValue(path: String, type: KType, onUnknownKeys: (Set
             else -> if (typeClass.java.isEnum) {
                 parseEnum(typeClass.java, getString(path))
             } else {
-                getConfig(path).parseAs(typeClass, onUnknownKeys, nestedPath?.let { "$it.$path" } ?: path)
+                getConfig(path).parseAs(typeClass, onUnknownKeys, nestedPath?.let { "$it.$path" } ?: path, baseDirectory = baseDirectory)
             }
         }
     } catch (e: ConfigException.Missing) {
@@ -155,6 +161,16 @@ private fun Config.getSingleValue(path: String, type: KType, onUnknownKeys: (Set
     }
 }
 
+private fun resolvePath(pathAsString: String, baseDirectory: Path?): Path {
+    val path = Paths.get(pathAsString)
+    return if (baseDirectory != null) {
+        // if baseDirectory been specified try resolving path against it. Note if `pathFromConfig` is an absolute path - this instruction has no effect.
+        baseDirectory.resolve(path)
+    } else {
+        path
+    }
+}
+
 private fun ConfigException.Missing.relative(path: String, nestedPath: String?): ConfigException.Missing {
     return when {
         nestedPath != null -> throw ConfigException.Missing("$nestedPath.$path", this)
@@ -162,7 +178,7 @@ private fun ConfigException.Missing.relative(path: String, nestedPath: String?):
     }
 }
 
-private fun Config.getCollectionValue(path: String, type: KType, onUnknownKeys: (Set<String>, logger: Logger) -> Unit, nestedPath: String? = null): Collection<Any> {
+private fun Config.getCollectionValue(path: String, type: KType, onUnknownKeys: (Set<String>, logger: Logger) -> Unit, nestedPath: String?, baseDirectory: Path?): Collection<Any> {
     val typeClass = type.jvmErasure
     require(typeClass == List::class || typeClass == Set::class) { "$typeClass is not supported" }
     val elementClass = type.arguments[0].type?.jvmErasure ?: throw IllegalArgumentException("Cannot work with star projection: $type")
@@ -179,7 +195,7 @@ private fun Config.getCollectionValue(path: String, type: KType, onUnknownKeys:
             LocalDate::class -> getStringList(path).map(LocalDate::parse)
             Instant::class -> getStringList(path).map(Instant::parse)
             NetworkHostAndPort::class -> getStringList(path).map(NetworkHostAndPort.Companion::parse)
-            Path::class -> getStringList(path).map { Paths.get(it) }
+            Path::class -> getStringList(path).map { resolvePath(it, baseDirectory) }
             URL::class -> getStringList(path).map(::URL)
             X500Principal::class -> getStringList(path).map(::X500Principal)
             UUID::class -> getStringList(path).map { UUID.fromString(it) }
@@ -188,7 +204,7 @@ private fun Config.getCollectionValue(path: String, type: KType, onUnknownKeys:
             else -> if (elementClass.java.isEnum) {
                 getStringList(path).map { parseEnum(elementClass.java, it) }
             } else {
-                getConfigList(path).map { it.parseAs(elementClass, onUnknownKeys) }
+                getConfigList(path).map { it.parseAs(elementClass, onUnknownKeys, baseDirectory = baseDirectory) }
             }
         }
     } catch (e: ConfigException.Missing) {
diff --git a/node/src/main/kotlin/net/corda/node/services/config/schema/v1/V1NodeConfigurationSpec.kt b/node/src/main/kotlin/net/corda/node/services/config/schema/v1/V1NodeConfigurationSpec.kt
index 0845879268..9eafb50bb2 100644
--- a/node/src/main/kotlin/net/corda/node/services/config/schema/v1/V1NodeConfigurationSpec.kt
+++ b/node/src/main/kotlin/net/corda/node/services/config/schema/v1/V1NodeConfigurationSpec.kt
@@ -69,10 +69,11 @@ internal object V1NodeConfigurationSpec : Configuration.Specification<NodeConfig
 
         val messagingServerExternal = configuration[messagingServerExternal] ?: Defaults.messagingServerExternal(configuration[messagingServerAddress])
         val database = configuration[database] ?: Defaults.database(configuration[devMode])
-        val cordappDirectories = configuration[cordappDirectories] ?: Defaults.cordappsDirectories(configuration[baseDirectory])
+        val baseDirectoryPath = configuration[baseDirectory]
+        val cordappDirectories = configuration[cordappDirectories] ?: Defaults.cordappsDirectories(baseDirectoryPath)
         val result = try {
             valid<NodeConfigurationImpl, Configuration.Validation.Error>(NodeConfigurationImpl(
-                    baseDirectory = configuration[baseDirectory],
+                    baseDirectory = baseDirectoryPath,
                     myLegalName = configuration[myLegalName],
                     emailAddress = configuration[emailAddress],
                     p2pAddress = configuration[p2pAddress],
@@ -116,7 +117,7 @@ internal object V1NodeConfigurationSpec : Configuration.Specification<NodeConfig
                     attachmentContentCacheSizeMegaBytes = configuration[attachmentContentCacheSizeMegaBytes],
                     h2port = configuration[h2port],
                     jarDirs = configuration[jarDirs],
-                    cordappDirectories = cordappDirectories,
+                    cordappDirectories = cordappDirectories.map { baseDirectoryPath.resolve(it) },
                     cordappSignerKeyFingerprintBlacklist = configuration[cordappSignerKeyFingerprintBlacklist]
             ))
         } catch (e: Exception) {
diff --git a/node/src/test/kotlin/net/corda/node/services/config/NodeConfigurationImplTest.kt b/node/src/test/kotlin/net/corda/node/services/config/NodeConfigurationImplTest.kt
index db21ad5778..266726f39b 100644
--- a/node/src/test/kotlin/net/corda/node/services/config/NodeConfigurationImplTest.kt
+++ b/node/src/test/kotlin/net/corda/node/services/config/NodeConfigurationImplTest.kt
@@ -5,6 +5,7 @@ import com.typesafe.config.ConfigFactory
 import com.typesafe.config.ConfigParseOptions
 import com.typesafe.config.ConfigValueFactory
 import net.corda.common.configuration.parsing.internal.Configuration
+import net.corda.core.internal.div
 import net.corda.core.internal.toPath
 import net.corda.core.utilities.NetworkHostAndPort
 import net.corda.core.utilities.seconds
@@ -16,7 +17,9 @@ import org.assertj.core.api.Assertions.assertThat
 import org.assertj.core.api.Assertions.assertThatThrownBy
 import org.junit.Assert.assertEquals
 import org.junit.Assert.assertNotNull
+import org.junit.Rule
 import org.junit.Test
+import org.junit.rules.TemporaryFolder
 import java.net.URI
 import java.net.URL
 import java.nio.file.Paths
@@ -25,6 +28,11 @@ import kotlin.test.assertFalse
 import kotlin.test.assertTrue
 
 class NodeConfigurationImplTest {
+
+    @Rule
+    @JvmField
+    val tempFolder = TemporaryFolder()
+
     @Test
     fun `can't have dev mode options if not in dev mode`() {
         val debugOptions = DevModeOptions()
@@ -192,6 +200,24 @@ class NodeConfigurationImplTest {
         assertThat(rawConfig.parseAsNodeConfiguration().isValid).isTrue()
     }
 
+    @Test
+    fun `relative path correctly parsed`() {
+        val rawConfig = ConfigFactory.parseResources("working-config.conf", ConfigParseOptions.defaults().setAllowMissing(false))
+
+        // Override base directory to have predictable experience on diff OSes
+        val finalConfig = configOf(
+                // Add substitution values here
+                "baseDirectory" to tempFolder.root.canonicalPath)
+                .withFallback(rawConfig)
+                .resolve()
+
+        val nodeConfiguration = finalConfig.parseAsNodeConfiguration()
+        assertThat(nodeConfiguration.isValid).isTrue()
+
+        val baseDirPath = tempFolder.root.toPath()
+        assertEquals(listOf(baseDirPath / "./myCorDapps1", baseDirPath / "./myCorDapps2"), nodeConfiguration.value().cordappDirectories)
+    }
+
     @Test
     fun `missing rpcSettings_adminAddress cause a graceful failure`() {
         var rawConfig = ConfigFactory.parseResources("working-config.conf", ConfigParseOptions.defaults().setAllowMissing(false))
diff --git a/node/src/test/resources/working-config.conf b/node/src/test/resources/working-config.conf
index 419b866013..ed1d05deb6 100644
--- a/node/src/test/resources/working-config.conf
+++ b/node/src/test/resources/working-config.conf
@@ -4,6 +4,7 @@ keyStorePassword = "cordacadevpass"
 trustStorePassword = "trustpass"
 crlCheckSoftFail = true
 baseDirectory = "/opt/corda"
+cordappDirectories = ["./myCorDapps1", "./myCorDapps2"]
 dataSourceProperties = {
     dataSourceClassName = org.h2.jdbcx.JdbcDataSource
     dataSource.url = "jdbc:h2:file:blah"