diff --git a/centaur/src/main/resources/standardTestCases/import_passwd.test b/centaur/src/main/resources/standardTestCases/import_passwd.test
new file mode 100644
index 00000000000..bed0c5f88a8
--- /dev/null
+++ b/centaur/src/main/resources/standardTestCases/import_passwd.test
@@ -0,0 +1,13 @@
+name: import_passwd
+testFormat: workflowfailure
+
+files {
+  workflow: import_passwd/import_passwd.wdl
+}
+
+metadata {
+  status: Failed
+  "failures.0.message": "Workflow input processing failed"
+  "failures.0.causedBy.0.message": "Failed to import workflow /etc/passwd.:\nBad import /etc/passwd: Failed to resolve '/etc/passwd' using resolver: 'http importer (no 'relative-to' origin)' (reason 1 of 1): Relative path"
+}
+
diff --git a/centaur/src/main/resources/standardTestCases/import_passwd/import_passwd.wdl b/centaur/src/main/resources/standardTestCases/import_passwd/import_passwd.wdl
new file mode 100644
index 00000000000..34b1617caaa
--- /dev/null
+++ b/centaur/src/main/resources/standardTestCases/import_passwd/import_passwd.wdl
@@ -0,0 +1,5 @@
+import "/etc/passwd" as whoa_there_buddy
+
+workflow foo {
+  call whoa_there_buddy.dont_do_that
+}
diff --git a/centaur/src/main/resources/standardTestCases/invalid_workflow_url.test b/centaur/src/main/resources/standardTestCases/invalid_workflow_url.test
index d306f156942..1aa315bf884 100644
--- a/centaur/src/main/resources/standardTestCases/invalid_workflow_url.test
+++ b/centaur/src/main/resources/standardTestCases/invalid_workflow_url.test
@@ -8,5 +8,5 @@ files {
 metadata {
   status: Failed
   "failures.0.message": "Workflow input processing failed"
-  "failures.0.causedBy.0.message": "Failed to resolve 'https://raw.githubusercontent.com/broadinstitute/cromwell/path_to_url_doesnt_exist' using resolver: 'relative to directory / (without escaping None)' (reason 1 of 1): Import file not found: https://raw.githubusercontent.com/broadinstitute/cromwell/path_to_url_doesnt_exist"
+  "failures.0.causedBy.0.message": "Failed to resolve 'https://raw.githubusercontent.com/broadinstitute/cromwell/path_to_url_doesnt_exist' using resolver: 'http importer (no 'relative-to' origin)' (reason 1 of 1): Failed to download https://raw.githubusercontent.com/broadinstitute/cromwell/path_to_url_doesnt_exist (reason 1 of 1): 400: Invalid request\n"
 }
diff --git a/common/src/main/scala/common/validation/Validation.scala b/common/src/main/scala/common/validation/Validation.scala
index 0af0f242dea..1cf111a4a31 100644
--- a/common/src/main/scala/common/validation/Validation.scala
+++ b/common/src/main/scala/common/validation/Validation.scala
@@ -78,7 +78,7 @@ object Validation {
   implicit class ValidationChecked[A](val e: Checked[A]) extends AnyVal {
     def unsafe(context: String): A = e.valueOr(errors => throw AggregatedMessageException(context, errors.toList))
 
-    def contextualizeErrors(s: String): Checked[A] = e.leftMap { errors =>
+    def contextualizeErrors(s: => String): Checked[A] = e.leftMap { errors =>
       val total = errors.size
       errors.zipWithIndex map { case (err, i) => s"Failed to $s (reason ${i + 1} of $total): $err" }
     }
diff --git a/engine/src/main/scala/cromwell/engine/workflow/SingleWorkflowRunnerActor.scala b/engine/src/main/scala/cromwell/engine/workflow/SingleWorkflowRunnerActor.scala
index 11b82727843..0c610066288 100644
--- a/engine/src/main/scala/cromwell/engine/workflow/SingleWorkflowRunnerActor.scala
+++ b/engine/src/main/scala/cromwell/engine/workflow/SingleWorkflowRunnerActor.scala
@@ -40,9 +40,7 @@ class SingleWorkflowRunnerActor(source: WorkflowSourceFilesCollection,
                                 gracefulShutdown: Boolean,
                                 abortJobsOnTerminate: Boolean
                                 )(implicit materializer: ActorMaterializer)
-  extends CromwellRootActor(gracefulShutdown, abortJobsOnTerminate) with LoggingFSM[RunnerState, SwraData] {
-
-  override val serverMode = false
+  extends CromwellRootActor(gracefulShutdown, abortJobsOnTerminate, false) with LoggingFSM[RunnerState, SwraData] {
 
   import SingleWorkflowRunnerActor._
   private val backoff = SimpleExponentialBackoff(1 second, 1 minute, 1.2)
diff --git a/engine/src/main/scala/cromwell/engine/workflow/lifecycle/materialization/MaterializeWorkflowDescriptorActor.scala b/engine/src/main/scala/cromwell/engine/workflow/lifecycle/materialization/MaterializeWorkflowDescriptorActor.scala
index e9bce53c799..74e85f79d72 100644
--- a/engine/src/main/scala/cromwell/engine/workflow/lifecycle/materialization/MaterializeWorkflowDescriptorActor.scala
+++ b/engine/src/main/scala/cromwell/engine/workflow/lifecycle/materialization/MaterializeWorkflowDescriptorActor.scala
@@ -1,7 +1,5 @@
 package cromwell.engine.workflow.lifecycle.materialization
 
-import java.nio.file.Paths
-
 import akka.actor.{ActorRef, FSM, LoggingFSM, Props, Status}
 import akka.pattern.pipe
 import cats.Monad
@@ -29,7 +27,7 @@ import cromwell.core.callcaching._
 import cromwell.core.io.AsyncIo
 import cromwell.core.labels.{Label, Labels}
 import cromwell.core.logging.WorkflowLogging
-import cromwell.core.path.{DefaultPath, PathBuilder}
+import cromwell.core.path.PathBuilder
 import cromwell.engine._
 import cromwell.engine.backend.CromwellBackends
 import cromwell.engine.language.CromwellLanguages
@@ -136,7 +134,6 @@ class MaterializeWorkflowDescriptorActor(serviceRegistryActor: ActorRef,
                                          ioActorProxy: ActorRef) extends LoggingFSM[MaterializeWorkflowDescriptorActorState, Unit] with LazyLogging with WorkflowLogging {
 
   import MaterializeWorkflowDescriptorActor._
-
   val tag = self.path.name
 
   val iOExecutionContext = context.system.dispatchers.lookup("akka.dispatchers.io-dispatcher")
@@ -232,12 +229,10 @@ class MaterializeWorkflowDescriptorActor(serviceRegistryActor: ActorRef,
                            resolvers: List[ImportResolver]): Checked[(WorkflowSource, List[ImportResolver])] = {
       (workflowSource, workflowUrl) match {
         case (Some(source), None) => (source, resolvers).validNelCheck
-        case (None, Some(url)) =>{
+        case (None, Some(url)) =>
           val compoundImportResolver: CheckedAtoB[ImportResolutionRequest, ResolvedImportBundle] = CheckedAtoB.firstSuccess(resolvers.map(_.resolver), s"resolve workflowUrl '$url'")
           val wfSourceAndResolvers: Checked[ResolvedImportBundle] = compoundImportResolver.run(ImportResolutionRequest(url, resolvers))
-
-          wfSourceAndResolvers map {v => (v.source, v.newResolvers) }
-        }
+          wfSourceAndResolvers map { v => (v.source, v.newResolvers) }
         case (Some(_), Some(_)) => "Both workflow source and url can't be supplied".invalidNelCheck
         case (None, None) => "Either workflow source or url has to be supplied".invalidNelCheck
       }
@@ -268,7 +263,9 @@ class MaterializeWorkflowDescriptorActor(serviceRegistryActor: ActorRef,
       errorOrParse(factory).flatMap(_.validateNamespace(sourceFiles, workflowSource, workflowOptions, importLocalFilesystem, workflowIdForLogging, engineIoFunctions, importResolvers))
     }
 
-    val localFilesystemResolvers = if (importLocalFilesystem) List(DirectoryResolver(DefaultPath(Paths.get("/")))) else List.empty
+    val localFilesystemResolvers =
+      if (importLocalFilesystem) DirectoryResolver.localFilesystemResolvers(None)
+      else List.empty
 
     val zippedResolverCheck: Parse[Option[ImportResolver]] = fromEither[IO](sourceFiles.importsZipFileOption match {
       case None => None.validNelCheck
diff --git a/engine/src/main/scala/cromwell/server/CromwellRootActor.scala b/engine/src/main/scala/cromwell/server/CromwellRootActor.scala
index 03c0d6ed260..a65e80f2b1d 100644
--- a/engine/src/main/scala/cromwell/server/CromwellRootActor.scala
+++ b/engine/src/main/scala/cromwell/server/CromwellRootActor.scala
@@ -52,7 +52,7 @@ import scala.util.{Failure, Success, Try}
   * READ THIS: If you add a "system-level" actor here, make sure to consider what should be its
   * position in the shutdown process and modify CromwellShutdown accordingly.
   */
-abstract class CromwellRootActor(gracefulShutdown: Boolean, abortJobsOnTerminate: Boolean)(implicit materializer: ActorMaterializer) extends Actor with ActorLogging with GracefulShutdownHelper {
+abstract class CromwellRootActor(gracefulShutdown: Boolean, abortJobsOnTerminate: Boolean, val serverMode: Boolean)(implicit materializer: ActorMaterializer) extends Actor with ActorLogging with GracefulShutdownHelper {
   import CromwellRootActor._
   
   // Make sure the filesystems are initialized at startup
@@ -65,8 +65,6 @@ abstract class CromwellRootActor(gracefulShutdown: Boolean, abortJobsOnTerminate
   private val workflowHeartbeatConfig = WorkflowHeartbeatConfig(config)
   logger.info("Workflow heartbeat configuration:\n{}", workflowHeartbeatConfig)
 
-  val serverMode: Boolean
-
   lazy val systemConfig = config.getConfig("system")
   lazy val serviceRegistryActor: ActorRef = context.actorOf(ServiceRegistryActor.props(config), "ServiceRegistryActor")
   lazy val numberOfWorkflowLogCopyWorkers = systemConfig.as[Option[Int]]("number-of-workflow-log-copy-workers").getOrElse(DefaultNumberOfWorkflowLogCopyWorkers)
diff --git a/engine/src/main/scala/cromwell/server/CromwellServer.scala b/engine/src/main/scala/cromwell/server/CromwellServer.scala
index 28d3bbbd2c5..af411f57da5 100644
--- a/engine/src/main/scala/cromwell/server/CromwellServer.scala
+++ b/engine/src/main/scala/cromwell/server/CromwellServer.scala
@@ -24,7 +24,7 @@ object CromwellServer {
 }
 
 class CromwellServerActor(cromwellSystem: CromwellSystem, gracefulShutdown: Boolean, abortJobsOnTerminate: Boolean)(override implicit val materializer: ActorMaterializer)
-  extends CromwellRootActor(gracefulShutdown, abortJobsOnTerminate)
+  extends CromwellRootActor(gracefulShutdown, abortJobsOnTerminate, serverMode = true)
     with CromwellApiService with CromwellInstrumentationActor
     with SwaggerService
     with ActorLogging {
@@ -32,8 +32,6 @@ class CromwellServerActor(cromwellSystem: CromwellSystem, gracefulShutdown: Bool
   override implicit val ec = context.dispatcher
   override def actorRefFactory: ActorContext = context
 
-  override val serverMode = true
-
   val webserviceConf = cromwellSystem.conf.getConfig("webservice")
   val interface = webserviceConf.getString("interface")
   val port = webserviceConf.getInt("port")
diff --git a/languageFactories/language-factory-core/src/main/scala/cromwell/languages/util/ImportResolver.scala b/languageFactories/language-factory-core/src/main/scala/cromwell/languages/util/ImportResolver.scala
index 769619b428f..346d43ec2c4 100644
--- a/languageFactories/language-factory-core/src/main/scala/cromwell/languages/util/ImportResolver.scala
+++ b/languageFactories/language-factory-core/src/main/scala/cromwell/languages/util/ImportResolver.scala
@@ -15,7 +15,7 @@ import common.transforms.CheckedAtoB
 import common.validation.ErrorOr._
 import common.validation.Checked._
 import common.validation.Validation._
-import cromwell.core.path.Path
+import cromwell.core.path.{DefaultPathBuilder, Path}
 import java.nio.file.{Path => NioPath}
 
 import wom.core.WorkflowSource
@@ -37,22 +37,42 @@ object ImportResolver {
     }
   }
 
-
   object DirectoryResolver {
-    def apply(directory: Path, allowEscapingDirectory: Boolean): DirectoryResolver = {
+    def apply(directory: Path, allowEscapingDirectory: Boolean, customName: Option[String]): DirectoryResolver = {
       val dontEscapeFrom = if (allowEscapingDirectory) None else Option(directory.toJava.getCanonicalPath)
-      DirectoryResolver(directory, dontEscapeFrom)
+      DirectoryResolver(directory, dontEscapeFrom, customName)
+    }
+
+    def localFilesystemResolvers(baseWdl: Option[Path]) = List(
+      DirectoryResolver(
+        DefaultPathBuilder.build(Paths.get(".")),
+        allowEscapingDirectory = true,
+        customName = None
+      ),
+      DirectoryResolver(
+        DefaultPathBuilder.build(Paths.get("/")),
+        allowEscapingDirectory = false,
+        customName = Some("entire local filesystem (relative to '/')")
+      )
+    ) ++ baseWdl.toList.map { rt =>
+      DirectoryResolver(
+        DefaultPathBuilder.build(Paths.get(rt.toAbsolutePath.toFile.getParent)),
+        allowEscapingDirectory = true,
+        customName = None
+      )
     }
   }
 
-  case class DirectoryResolver(directory: Path, dontEscapeFrom: Option[String] = None) extends ImportResolver {
-    lazy val absolutePathToDirectory = directory.toJava.getCanonicalPath
+  case class DirectoryResolver(directory: Path,
+                               dontEscapeFrom: Option[String] = None,
+                               customName: Option[String]) extends ImportResolver {
+    lazy val absolutePathToDirectory: String = directory.toJava.getCanonicalPath
 
     override def innerResolver(path: String, currentResolvers: List[ImportResolver]): Checked[ResolvedImportBundle] = {
 
       def updatedResolverSet(oldRootDirectory: Path, newRootDirectory: Path, current: List[ImportResolver]): List[ImportResolver] = {
         current map {
-          case d if d == this => DirectoryResolver(newRootDirectory, dontEscapeFrom)
+          case d if d == this => DirectoryResolver(newRootDirectory, dontEscapeFrom, customName)
           case other => other
         }
       }
@@ -63,7 +83,7 @@ object ImportResolver {
           if (file.exists) {
             File(absolutePathToFile).contentAsString.validNel
           } else {
-            s"Import file not found: $path".invalidNel
+            s"File not found: $path".invalidNel
           }
         }
       }
@@ -92,20 +112,35 @@ object ImportResolver {
       _ <- checkLocation(abs, path)
     } yield abs
 
-    override def name: String = s"relative to directory $absolutePathToDirectory (without escaping $dontEscapeFrom)"
+    override lazy val name: String = (customName, dontEscapeFrom) match {
+      case (Some(custom), _) => custom
+      case (None, Some(dontEscapePath)) =>
+        val dontEscapeFromDirname = Paths.get(dontEscapePath).getFileName.toString
+        val shortPathToDirectory = absolutePathToDirectory.stripPrefix(dontEscapePath)
+
+        val relativePathToDontEscapeFrom = s"[...]/$dontEscapeFromDirname"
+        val relativePathToDirectory = s"$relativePathToDontEscapeFrom$shortPathToDirectory"
+
+        s"relative to directory $relativePathToDirectory (without escaping $relativePathToDontEscapeFrom)"
+      case (None, None) =>
+        val shortPathToDirectory = Paths.get(absolutePathToDirectory).toFile.getCanonicalFile.toPath.getFileName.toString
+        s"relative to directory [...]/$shortPathToDirectory (escaping allowed)"
+    }
   }
 
   def zippedImportResolver(zippedImports: Array[Byte]): ErrorOr[ImportResolver] = {
     LanguageFactoryUtil.validateImportsDirectory(zippedImports) map { dir =>
-      DirectoryResolver(dir, Option(dir.toJava.getCanonicalPath))
+      DirectoryResolver(dir, Option(dir.toJava.getCanonicalPath), None)
     }
   }
 
   case class HttpResolver(relativeTo: Option[String] = None, headers: Map[String, String] = Map.empty) extends ImportResolver {
     import HttpResolver._
 
-    override def name: String = {
-      s"http importer${relativeTo map { r => s" (relative to $r)" } getOrElse ""}"
+    override def name: String = relativeTo match {
+      case Some(relativeToPath) => s"http importer (relative to $relativeToPath)"
+      case None => "http importer (no 'relative-to' origin)"
+
     }
 
     def newResolverList(newRoot: String): List[ImportResolver] = {
@@ -122,7 +157,7 @@ object ImportResolver {
         else canonicalize(s"${relativeToValue.stripSuffix("/")}/$str").validNelCheck
       case None =>
         if (str.startsWith("http")) canonicalize(str).validNelCheck
-        else s"Cannot import '$str' relative to nothing".invalidNelCheck
+        else "Relative path".invalidNelCheck
     }
 
     override def innerResolver(str: String, currentResolvers: List[ImportResolver]): Checked[ResolvedImportBundle] = {
@@ -147,10 +182,13 @@ object ImportResolver {
   }
 
   object HttpResolver {
+
     import common.util.IntrospectableLazy
     import common.util.IntrospectableLazy._
 
-    val sttpBackend: IntrospectableLazy[SttpBackend[IO, Nothing]] = lazily { AsyncHttpClientCatsBackend[IO]() }
+    val sttpBackend: IntrospectableLazy[SttpBackend[IO, Nothing]] = lazily {
+      AsyncHttpClientCatsBackend[IO]()
+    }
 
     def closeBackendIfNecessary() = if (sttpBackend.exists) sttpBackend.close()
 
diff --git a/languageFactories/language-factory-core/src/test/scala/cromwell/languages/util/ImportResolverSpec.scala b/languageFactories/language-factory-core/src/test/scala/cromwell/languages/util/ImportResolverSpec.scala
index 994b3c6c0a5..1142768649c 100644
--- a/languageFactories/language-factory-core/src/test/scala/cromwell/languages/util/ImportResolverSpec.scala
+++ b/languageFactories/language-factory-core/src/test/scala/cromwell/languages/util/ImportResolverSpec.scala
@@ -65,7 +65,7 @@ class ImportResolverSpec extends FlatSpec with Matchers {
 
   behavior of "directory resolver from root"
 
-  val rootDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/")))
+  val rootDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/")), customName = None)
 
   it should "resolve a random path" in {
     val pathToLookup = rootDirectoryResolver.resolveAndMakeAbsolute("/path/to/file.wdl")
@@ -74,7 +74,7 @@ class ImportResolverSpec extends FlatSpec with Matchers {
 
   behavior of "unprotected relative directory resolver"
 
-  val relativeDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/path/to/imports/")))
+  val relativeDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/path/to/imports/")), customName = None)
 
   it should "resolve an absolute path" in {
     val pathToLookup = relativeDirectoryResolver.resolveAndMakeAbsolute("/path/to/file.wdl")
@@ -88,7 +88,7 @@ class ImportResolverSpec extends FlatSpec with Matchers {
 
   behavior of "protected relative directory resolver"
 
-  val protectedRelativeDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/path/to/imports/")), Some("/path/to/imports/"))
+  val protectedRelativeDirectoryResolver = DirectoryResolver(DefaultPath(Paths.get("/path/to/imports/")), Some("/path/to/imports/"), customName = None)
 
   it should "resolve a good relative path" in {
     val pathToLookup = protectedRelativeDirectoryResolver.resolveAndMakeAbsolute("path/to/file.wdl")
diff --git a/server/src/test/scala/cromwell/CromwellTestKitSpec.scala b/server/src/test/scala/cromwell/CromwellTestKitSpec.scala
index 6304958a058..567f7fe354c 100644
--- a/server/src/test/scala/cromwell/CromwellTestKitSpec.scala
+++ b/server/src/test/scala/cromwell/CromwellTestKitSpec.scala
@@ -232,8 +232,7 @@ object CromwellTestKitSpec {
     ServiceRegistryActorSystem.actorOf(ServiceRegistryActor.props(ConfigFactory.load()), "ServiceRegistryActor")
   }
 
-  class TestCromwellRootActor(config: Config)(implicit materializer: ActorMaterializer) extends CromwellRootActor(false, false) {
-    override val serverMode = true
+  class TestCromwellRootActor(config: Config)(implicit materializer: ActorMaterializer) extends CromwellRootActor(false, false, serverMode = true) {
     override lazy val serviceRegistryActor = ServiceRegistryActorInstance
     override lazy val workflowStore = new InMemoryWorkflowStore
     def submitWorkflow(sources: WorkflowSourceFilesWithoutImports): WorkflowId = {
diff --git a/server/src/test/scala/cromwell/engine/workflow/lifecycle/MaterializeWorkflowDescriptorActorSpec.scala b/server/src/test/scala/cromwell/engine/workflow/lifecycle/MaterializeWorkflowDescriptorActorSpec.scala
index 051bee0ea7a..d6f41af8ec3 100644
--- a/server/src/test/scala/cromwell/engine/workflow/lifecycle/MaterializeWorkflowDescriptorActorSpec.scala
+++ b/server/src/test/scala/cromwell/engine/workflow/lifecycle/MaterializeWorkflowDescriptorActorSpec.scala
@@ -275,7 +275,10 @@ class MaterializeWorkflowDescriptorActorSpec extends CromwellTestKitWordSpec wit
       within(Timeout) {
         expectMsgPF() {
           case MaterializeWorkflowDescriptorFailureResponse(reason) =>
-            reason.getMessage should startWith("Workflow input processing failed:\nFailed to resolve 'https://raw.githubusercontent.com/broadinstitute/cromwell/develop/my_workflow' using resolver: 'http importer' (reason 1 of 1): Failed to download https://raw.githubusercontent.com/broadinstitute/cromwell/develop/my_workflow (reason 1 of 1): 404: Not Found")
+            reason.getMessage should startWith(
+              """Workflow input processing failed:
+                |Failed to resolve 'https://raw.githubusercontent.com/broadinstitute/cromwell/develop/my_workflow' using resolver: 'http importer (no 'relative-to' origin)' (reason 1 of 1): Failed to download https://raw.githubusercontent.com/broadinstitute/cromwell/develop/my_workflow (reason 1 of 1): 404: Not Found"""
+                .stripMargin)
           case _: MaterializeWorkflowDescriptorSuccessResponse => fail("This materialization should not have succeeded!")
           case unknown =>
             fail(s"Unexpected materialization response: $unknown")
diff --git a/womtool/src/main/scala/womtool/input/WomGraphMaker.scala b/womtool/src/main/scala/womtool/input/WomGraphMaker.scala
index 561477a25da..05a3e691557 100644
--- a/womtool/src/main/scala/womtool/input/WomGraphMaker.scala
+++ b/womtool/src/main/scala/womtool/input/WomGraphMaker.scala
@@ -5,7 +5,7 @@ import java.nio.file.{Files, Paths}
 import com.typesafe.config.ConfigFactory
 import common.Checked
 import common.validation.Validation._
-import cromwell.core.path.{DefaultPathBuilder, Path}
+import cromwell.core.path.Path
 import cromwell.languages.LanguageFactory
 import cromwell.languages.util.ImportResolver._
 import languages.cwl.CwlV1_0LanguageFactory
@@ -24,19 +24,8 @@ object WomGraphMaker {
   def getBundle(mainFile: Path): Checked[WomBundle] = getBundleAndFactory(mainFile).map(_._1)
 
   private def getBundleAndFactory(mainFile: Path): Checked[(WomBundle, LanguageFactory)] = {
-    // Resolves for:
-    // - Where we run from
-    // - Where the file is
-    lazy val importResolvers: List[ImportResolver] = List(
-      DirectoryResolver(
-        DefaultPathBuilder.build(Paths.get(".")),
-        allowEscapingDirectory = false),
-      DirectoryResolver(
-        DefaultPathBuilder.build(Paths.get(mainFile.toAbsolutePath.toFile.getParent)),
-        allowEscapingDirectory = true
-      ),
-      HttpResolver()
-    )
+    lazy val importResolvers: List[ImportResolver] =
+      DirectoryResolver.localFilesystemResolvers(Some(mainFile)) :+ HttpResolver(relativeTo = None)
 
     readFile(mainFile.toAbsolutePath.pathAsString) flatMap { mainFileContents =>
       val languageFactory =
diff --git a/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/bad_import.wdl b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/bad_import.wdl
new file mode 100644
index 00000000000..ec208e4fbb2
--- /dev/null
+++ b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/bad_import.wdl
@@ -0,0 +1,7 @@
+version 1.0
+
+import "sub_dir/bad_import.wdl" as found_but_invalid
+
+workflow foo {
+  call found_but_invalid.call_a_bad_thing
+}
diff --git a/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/error.txt b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/error.txt
new file mode 100644
index 00000000000..687577d2b2d
--- /dev/null
+++ b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/error.txt
@@ -0,0 +1,4 @@
+Failed to import 'sub_dir/bad_import.wdl' (reason 1 of 4): Failed to import 'not/a/file.wdl' (reason 1 of 4): Failed to resolve 'not/a/file.wdl' using resolver: 'relative to directory [...]/cromwell (escaping allowed)' (reason 1 of 1): File not found: not/a/file.wdl
+Failed to import 'sub_dir/bad_import.wdl' (reason 2 of 4): Failed to import 'not/a/file.wdl' (reason 2 of 4): Failed to resolve 'not/a/file.wdl' using resolver: 'entire local filesystem (relative to '/')' (reason 1 of 1): File not found: not/a/file.wdl
+Failed to import 'sub_dir/bad_import.wdl' (reason 3 of 4): Failed to import 'not/a/file.wdl' (reason 3 of 4): Failed to resolve 'not/a/file.wdl' using resolver: 'relative to directory [...]/sub_dir (escaping allowed)' (reason 1 of 1): File not found: not/a/file.wdl
+Failed to import 'sub_dir/bad_import.wdl' (reason 4 of 4): Failed to import 'not/a/file.wdl' (reason 4 of 4): Failed to resolve 'not/a/file.wdl' using resolver: 'http importer (no 'relative-to' origin)' (reason 1 of 1): Relative path
diff --git a/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/sub_dir/bad_import.wdl b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/sub_dir/bad_import.wdl
new file mode 100644
index 00000000000..a66aad2390a
--- /dev/null
+++ b/womtool/src/test/resources/validate/wdl_draft3/invalid/bad_import/sub_dir/bad_import.wdl
@@ -0,0 +1,7 @@
+version 1.0
+
+import "not/a/file.wdl" as not_a_file
+
+workflow call_a_bad_thing {
+  call not_a_file.not_a_task
+}