diff --git a/plans/objchange/objchange.go b/plans/objchange/objchange.go
index 5a8af1481f..ab16f68a4b 100644
--- a/plans/objchange/objchange.go
+++ b/plans/objchange/objchange.go
@@ -333,8 +333,9 @@ func setElementCompareValue(schema *configschema.Block, v cty.Value, isConfig bo
 	}
 
 	for name, blockType := range schema.BlockTypes {
-		switch blockType.Nesting {
+		elementType := blockType.Block.ImpliedType()
 
+		switch blockType.Nesting {
 		case configschema.NestingSingle, configschema.NestingGroup:
 			attrs[name] = setElementCompareValue(&blockType.Block, v.GetAttr(name), isConfig)
 
@@ -344,32 +345,44 @@ func setElementCompareValue(schema *configschema.Block, v cty.Value, isConfig bo
 				attrs[name] = cv
 				continue
 			}
+
 			if l := cv.LengthInt(); l > 0 {
 				elems := make([]cty.Value, 0, l)
 				for it := cv.ElementIterator(); it.Next(); {
 					_, ev := it.Element()
 					elems = append(elems, setElementCompareValue(&blockType.Block, ev, isConfig))
 				}
-				if blockType.Nesting == configschema.NestingSet {
+
+				switch {
+				case blockType.Nesting == configschema.NestingSet:
 					// SetValEmpty would panic if given elements that are not
 					// all of the same type, but that's guaranteed not to
 					// happen here because our input value was _already_ a
 					// set and we've not changed the types of any elements here.
 					attrs[name] = cty.SetVal(elems)
-				} else {
+
+				// NestingList cases
+				case elementType.HasDynamicTypes():
 					attrs[name] = cty.TupleVal(elems)
+				default:
+					attrs[name] = cty.ListVal(elems)
 				}
 			} else {
-				if blockType.Nesting == configschema.NestingSet {
-					attrs[name] = cty.SetValEmpty(blockType.Block.ImpliedType())
-				} else {
+				switch {
+				case blockType.Nesting == configschema.NestingSet:
+					attrs[name] = cty.SetValEmpty(elementType)
+
+				// NestingList cases
+				case elementType.HasDynamicTypes():
 					attrs[name] = cty.EmptyTupleVal
+				default:
+					attrs[name] = cty.ListValEmpty(elementType)
 				}
 			}
 
 		case configschema.NestingMap:
 			cv := v.GetAttr(name)
-			if cv.IsNull() || !cv.IsKnown() {
+			if cv.IsNull() || !cv.IsKnown() || cv.LengthInt() == 0 {
 				attrs[name] = cv
 				continue
 			}
@@ -378,7 +391,13 @@ func setElementCompareValue(schema *configschema.Block, v cty.Value, isConfig bo
 				kv, ev := it.Element()
 				elems[kv.AsString()] = setElementCompareValue(&blockType.Block, ev, isConfig)
 			}
-			attrs[name] = cty.ObjectVal(elems)
+
+			switch {
+			case elementType.HasDynamicTypes():
+				attrs[name] = cty.ObjectVal(elems)
+			default:
+				attrs[name] = cty.MapVal(elems)
+			}
 
 		default:
 			// Should never happen, since the above cases are comprehensive.
diff --git a/plans/objchange/objchange_test.go b/plans/objchange/objchange_test.go
index 97f749acae..065e4add88 100644
--- a/plans/objchange/objchange_test.go
+++ b/plans/objchange/objchange_test.go
@@ -440,7 +440,7 @@ func TestProposedNewObject(t *testing.T) {
 					}),
 					"b": cty.ObjectVal(map[string]cty.Value{
 						"bar": cty.StringVal("blep"),
-						"baz": cty.StringVal("boot"),
+						"baz": cty.ListVal([]cty.Value{cty.StringVal("boot")}),
 					}),
 				}),
 			}),
@@ -452,7 +452,7 @@ func TestProposedNewObject(t *testing.T) {
 					}),
 					"c": cty.ObjectVal(map[string]cty.Value{
 						"bar": cty.StringVal("bosh"),
-						"baz": cty.NullVal(cty.String),
+						"baz": cty.NullVal(cty.List(cty.String)),
 					}),
 				}),
 			}),
@@ -464,7 +464,7 @@ func TestProposedNewObject(t *testing.T) {
 					}),
 					"c": cty.ObjectVal(map[string]cty.Value{
 						"bar": cty.StringVal("bosh"),
-						"baz": cty.NullVal(cty.String),
+						"baz": cty.NullVal(cty.List(cty.String)),
 					}),
 				}),
 			}),
@@ -572,6 +572,288 @@ func TestProposedNewObject(t *testing.T) {
 				}),
 			}),
 		},
+		"nested list in set": {
+			&configschema.Block{
+				BlockTypes: map[string]*configschema.NestedBlock{
+					"foo": {
+						Nesting: configschema.NestingSet,
+						Block: configschema.Block{
+							BlockTypes: map[string]*configschema.NestedBlock{
+								"bar": {
+									Nesting: configschema.NestingList,
+									Block: configschema.Block{
+										Attributes: map[string]*configschema.Attribute{
+											"baz": {
+												Type: cty.String,
+											},
+											"qux": {
+												Type:     cty.String,
+												Computed: true,
+												Optional: true,
+											},
+										},
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("beep"),
+								"qux": cty.StringVal("boop"),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("beep"),
+								"qux": cty.NullVal(cty.String),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("beep"),
+								"qux": cty.StringVal("boop"),
+							}),
+						}),
+					}),
+				}),
+			}),
+		},
+		"empty nested list in set": {
+			&configschema.Block{
+				BlockTypes: map[string]*configschema.NestedBlock{
+					"foo": {
+						Nesting: configschema.NestingSet,
+						Block: configschema.Block{
+							BlockTypes: map[string]*configschema.NestedBlock{
+								"bar": {
+									Nesting: configschema.NestingList,
+									Block:   configschema.Block{},
+								},
+							},
+						},
+					},
+				},
+			},
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListValEmpty((&configschema.Block{}).ImpliedType()),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListValEmpty((&configschema.Block{}).ImpliedType()),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ListValEmpty((&configschema.Block{}).ImpliedType()),
+					}),
+				}),
+			}),
+		},
+		"nested list with dynamic in set": {
+			&configschema.Block{
+				BlockTypes: map[string]*configschema.NestedBlock{
+					"foo": {
+						Nesting: configschema.NestingSet,
+						Block: configschema.Block{
+							BlockTypes: map[string]*configschema.NestedBlock{
+								"bar": {
+									Nesting: configschema.NestingList,
+									Block: configschema.Block{
+										Attributes: map[string]*configschema.Attribute{
+											"baz": {
+												Type: cty.DynamicPseudoType,
+											},
+										},
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.TupleVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.TupleVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.TupleVal([]cty.Value{
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+							cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+		},
+		"nested map with dynamic in set": {
+			&configschema.Block{
+				BlockTypes: map[string]*configschema.NestedBlock{
+					"foo": {
+						Nesting: configschema.NestingSet,
+						Block: configschema.Block{
+							BlockTypes: map[string]*configschema.NestedBlock{
+								"bar": {
+									Nesting: configschema.NestingMap,
+									Block: configschema.Block{
+										Attributes: map[string]*configschema.Attribute{
+											"baz": {
+												Type:     cty.DynamicPseudoType,
+												Optional: true,
+											},
+										},
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ObjectVal(map[string]cty.Value{
+							"bing": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+							"bang": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ObjectVal(map[string]cty.Value{
+							"bing": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.ObjectVal(map[string]cty.Value{
+							"bing": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.ListVal([]cty.Value{cty.StringVal("true")}),
+							}),
+						}),
+					}),
+				}),
+			}),
+		},
+		"empty nested map in set": {
+			&configschema.Block{
+				BlockTypes: map[string]*configschema.NestedBlock{
+					"foo": {
+						Nesting: configschema.NestingSet,
+						Block: configschema.Block{
+							BlockTypes: map[string]*configschema.NestedBlock{
+								"bar": {
+									Nesting: configschema.NestingMap,
+									Block: configschema.Block{
+										Attributes: map[string]*configschema.Attribute{
+											"baz": {
+												Type:     cty.String,
+												Optional: true,
+											},
+										},
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.MapValEmpty(cty.Object(map[string]cty.Type{
+							"baz": cty.String,
+						})),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.MapVal(map[string]cty.Value{
+							"bing": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+						}),
+					}),
+				}),
+			}),
+			cty.ObjectVal(map[string]cty.Value{
+				"foo": cty.SetVal([]cty.Value{
+					cty.ObjectVal(map[string]cty.Value{
+						"bar": cty.MapVal(map[string]cty.Value{
+							"bing": cty.ObjectVal(map[string]cty.Value{
+								"baz": cty.StringVal("true"),
+							}),
+						}),
+					}),
+				}),
+			}),
+		},
 	}
 
 	for name, test := range tests {