diff --git a/core-macros/src/main/scala/sbt/internal/util/appmacro/ContextUtil.scala b/core-macros/src/main/scala/sbt/internal/util/appmacro/ContextUtil.scala
index f6dbf5894..993072ab9 100644
--- a/core-macros/src/main/scala/sbt/internal/util/appmacro/ContextUtil.scala
+++ b/core-macros/src/main/scala/sbt/internal/util/appmacro/ContextUtil.scala
@@ -109,12 +109,14 @@ final class ContextUtil[C <: blackbox.Context](val ctx: C) {
   def illegalReference(defs: collection.Set[Symbol], sym: Symbol): Boolean =
     sym != null && sym != NoSymbol && defs.contains(sym)
 
+  type PropertyChecker = (String, Type, Tree) => Boolean
+
   /**
    * A function that checks the provided tree for illegal references to M instances defined in the
    *  expression passed to the macro and for illegal dereferencing of M instances.
    */
   def checkReferences(defs: collection.Set[Symbol],
-                      isWrapper: (String, Type, Tree) => Boolean): Tree => Unit = {
+                      isWrapper: PropertyChecker): Tree => Unit = {
     case s @ ApplyTree(TypeApply(Select(_, nme), tpe :: Nil), qual :: Nil) =>
       if (isWrapper(nme.decodedName.toString, tpe.tpe, qual))
         ctx.error(s.pos, DynamicDependencyError)
@@ -123,6 +125,28 @@ final class ContextUtil[C <: blackbox.Context](val ctx: C) {
     case _ => ()
   }
 
+  class TaskMacroViolationDiscovery(isInvalid: PropertyChecker) extends Traverser {
+    var insideIf: Boolean = false
+    override def traverse(tree: ctx.universe.Tree): Unit = {
+      tree match {
+        case If(condition, thenp, elsep) =>
+          super.traverse(condition)
+          insideIf = true
+          super.traverse(thenp)
+          super.traverse(elsep)
+          insideIf = false
+        case s @ ApplyTree(TypeApply(Select(_, nme), tpe :: Nil), qual :: Nil) =>
+          if (insideIf && isInvalid(nme.decodedName.toString, tpe.tpe, qual)) {
+            ctx.error(s.pos, "DSL error: a task value cannot be obtained inside if.")
+          }
+        case _ => super.traverse(tree)
+      }
+    }
+  }
+
+  def checkMacroViolations(tree: Tree, isInvalid: PropertyChecker) =
+    new TaskMacroViolationDiscovery(isInvalid).traverse(tree)
+
   /** Constructs a ValDef with a parameter modifier, a unique name, with the provided Type and with an empty rhs. */
   def freshMethodParameter(tpe: Type): ValDef =
     ValDef(parameterModifiers, freshTermName("p"), TypeTree(tpe), EmptyTree)
diff --git a/core-macros/src/main/scala/sbt/internal/util/appmacro/Instance.scala b/core-macros/src/main/scala/sbt/internal/util/appmacro/Instance.scala
index e5a2fcbf3..9a36e3ff8 100644
--- a/core-macros/src/main/scala/sbt/internal/util/appmacro/Instance.scala
+++ b/core-macros/src/main/scala/sbt/internal/util/appmacro/Instance.scala
@@ -86,6 +86,8 @@ object Instance {
       nt: c.WeakTypeTag[N[T]],
       it: c.TypeTag[i.type]
   ): c.Expr[i.M[N[T]]] = {
+    println("STARTING CONTIMPL")
+    println("=================")
     import c.universe.{ Apply => ApplyTree, _ }
 
     val util = ContextUtil[c.type](c)
@@ -97,6 +99,8 @@ object Instance {
       case Left(l)  => (l.tree, nt.tpe.dealias)
       case Right(r) => (r.tree, mttpe)
     }
+    println("TREE TYPE")
+    println(treeType)
     // the Symbol for the anonymous function passed to the appropriate Instance.map/flatMap/pure method
     // this Symbol needs to be known up front so that it can be used as the owner of synthetic vals
     val functionSym = util.functionSymbol(tree.pos)
@@ -183,9 +187,17 @@ object Instance {
     }
 
     // applies the transformation
+    println("TREE")
+    println(tree)
+    import util.PropertyChecker
+    val isInvalid: PropertyChecker =
+      (s: String, tpe: Type, tree: Tree) => t.isLeft && convert.asPredicate(c).apply(s, tpe, tree)
+    util.checkMacroViolations(tree, isInvalid)
     val tx = util.transformWrappers(tree, (n, tpe, t, replace) => sub(n, tpe, t, replace))
     // resetting attributes must be: a) local b) done here and not wider or else there are obscure errors
     val tr = makeApp(inner(tx))
+    println("FINAL TREE")
+    println(tr)
     c.Expr[i.M[N[T]]](tr)
   }
 
diff --git a/main-settings/src/test/scala/sbt/std/TaskPosSpec.scala b/main-settings/src/test/scala/sbt/std/TaskPosSpec.scala
new file mode 100644
index 000000000..c97ce92ba
--- /dev/null
+++ b/main-settings/src/test/scala/sbt/std/TaskPosSpec.scala
@@ -0,0 +1,29 @@
+package sbt.std
+
+class TaskPosSpec {
+  // Dynamic tasks can have task invocations inside if branches
+  locally {
+    import sbt._
+    import sbt.Def._
+    val foo = taskKey[String]("")
+    val bar = taskKey[String]("")
+    var condition = true
+    val baz = Def.taskDyn[String] {
+      if (condition) foo
+      else bar
+    }
+  }
+
+  // Dynamic settings can have setting invocations inside if branches
+  locally {
+    import sbt._
+    import sbt.Def._
+    val foo = settingKey[String]("")
+    val bar = settingKey[String]("")
+    var condition = true
+    val baz = Def.settingDyn[String] {
+      if (condition) foo
+      else bar
+    }
+  }
+}
diff --git a/main-settings/src/test/scala/sbt/std/TestUtil.scala b/main-settings/src/test/scala/sbt/std/TestUtil.scala
index 09365ba52..34b6a1b3b 100644
--- a/main-settings/src/test/scala/sbt/std/TestUtil.scala
+++ b/main-settings/src/test/scala/sbt/std/TestUtil.scala
@@ -8,18 +8,7 @@ package sbt.std
 import scala.reflect._
 
 object TestUtil {
-  import tools.reflect.{ ToolBox, ToolBoxError }
-
-  def intercept[T <: Throwable: ClassTag](test: => Any): T = {
-    try {
-      test
-      throw new Exception(s"Expected exception ${classTag[T]}")
-    } catch {
-      case t: Throwable =>
-        if (classTag[T].runtimeClass != t.getClass) throw t
-        else t.asInstanceOf[T]
-    }
-  }
+  import tools.reflect.ToolBox
 
   def eval(code: String, compileOptions: String = ""): Any = {
     val tb = mkToolbox(compileOptions)
@@ -38,18 +27,4 @@ object TestUtil {
     val completeSporesCoreClasspath = classpathFile.getLines.mkString
     completeSporesCoreClasspath
   }
-
-  def expectError(errorSnippet: String,
-                  compileOptions: String = "-Xmacro-settings:debug-spores",
-                  baseCompileOptions: String = s"-cp $toolboxClasspath")(code: String): Unit = {
-    val errorMessage = intercept[ToolBoxError] {
-      eval(code, s"$compileOptions $baseCompileOptions")
-    }.getMessage
-    val userMessage =
-      s"""
-         |FOUND: $errorMessage
-         |EXPECTED: $errorSnippet
-      """.stripMargin
-    assert(errorMessage.contains(errorSnippet), userMessage)
-  }
 }
diff --git a/main-settings/src/test/scala/sbt/std/neg/TaskNegSpec.scala b/main-settings/src/test/scala/sbt/std/neg/TaskNegSpec.scala
new file mode 100644
index 000000000..17f16d3f8
--- /dev/null
+++ b/main-settings/src/test/scala/sbt/std/neg/TaskNegSpec.scala
@@ -0,0 +1,42 @@
+package sbt.std.neg
+
+import org.scalatest.FunSuite
+import sbt.std.TestUtil._
+
+class TaskNegSpec extends FunSuite {
+  import tools.reflect.ToolBoxError
+  def expectError(errorSnippet: String,
+                  compileOptions: String = "-Xmacro-settings:debug-spores",
+                  baseCompileOptions: String = s"-cp $toolboxClasspath")(code: String) = {
+    val errorMessage = intercept[ToolBoxError] {
+      eval(code, s"$compileOptions $baseCompileOptions")
+      println("ERROR: The snippet compiled successfully.")
+    }.getMessage
+    val userMessage =
+      s"""
+         |FOUND: $errorMessage
+         |EXPECTED: $errorSnippet
+      """.stripMargin
+    println(userMessage)
+    assert(errorMessage.contains(errorSnippet), userMessage)
+  }
+
+  test("Fail on task invocation inside if of regular task") {
+
+    expectError("DSL error: a task value cannot be obtained inside if.") {
+      """
+        |import sbt._
+        |import sbt.Def._
+        |
+        |val fooNeg = taskKey[String]("")
+        |val barNeg = taskKey[String]("")
+        |var condition = true
+        |
+        |val bazNeg: Initialize[Task[String]] = Def.task[String] {
+        |  if (condition) fooNeg.value
+        |  else barNeg.value
+        |}
+      """.stripMargin
+    }
+  }
+}
diff --git a/project/Dependencies.scala b/project/Dependencies.scala
index 7d918eaaf..468402eb1 100644
--- a/project/Dependencies.scala
+++ b/project/Dependencies.scala
@@ -110,6 +110,7 @@ object Dependencies {
 
   val sjsonNewScalaJson = "com.eed3si9n" %% "sjson-new-scalajson" % "0.7.0"
 
+  val scalatest = "org.scalatest" %% "scalatest" % "3.0.1"
   val scalaCheck = "org.scalacheck" %% "scalacheck" % "1.13.4"
   val specs2 = "org.specs2" %% "specs2" % "2.4.17"
   val junit = "junit" % "junit" % "4.11"
diff --git a/project/NightlyPlugin.scala b/project/NightlyPlugin.scala
index 893410d0b..58c1917dc 100644
--- a/project/NightlyPlugin.scala
+++ b/project/NightlyPlugin.scala
@@ -10,7 +10,7 @@ object NightlyPlugin extends AutoPlugin {
     val includeTestDependencies = settingKey[Boolean]("Doesn't declare test dependencies.")
 
     def testDependencies = libraryDependencies ++= (
-      if (includeTestDependencies.value) Seq(scalaCheck % Test, specs2 % Test, junit % Test)
+      if (includeTestDependencies.value) Seq(scalaCheck % Test, specs2 % Test, junit % Test, scalatest % Test)
       else Seq()
     )
   }