diff --git a/pkg/internal/tests/cross-tests/diff_cross_test.go b/pkg/internal/tests/cross-tests/diff_cross_test.go
index f47850243a..7536ea629f 100644
--- a/pkg/internal/tests/cross-tests/diff_cross_test.go
+++ b/pkg/internal/tests/cross-tests/diff_cross_test.go
@@ -1625,6 +1625,14 @@ func TestBlockCollectionElementForceNew(t *testing.T) {
 	})
 }
 
+type diffTestOutput struct {
+	initialValue cty.Value
+	changeValue  cty.Value
+	tfOut        string
+	pulumiOut    string
+	detailedDiff map[string]any
+}
+
 func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 	t.Parallel()
 
@@ -1649,14 +1657,6 @@ func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 		},
 	}
 
-	type testOutput struct {
-		initialValue cty.Value
-		changeValue  cty.Value
-		tfOut        string
-		pulumiOut    string
-		detailedDiff map[string]any
-	}
-
 	t.Run("no change", func(t *testing.T) {
 		t.Parallel()
 		initialValue := cty.ObjectVal(map[string]cty.Value{})
@@ -1667,7 +1667,7 @@ func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 			Config2:  changeValue,
 		})
 
-		autogold.ExpectFile(t, testOutput{
+		autogold.ExpectFile(t, diffTestOutput{
 			initialValue: initialValue,
 			changeValue:  changeValue,
 			tfOut:        diff.TFOut,
@@ -1686,7 +1686,7 @@ func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 			Config2:  changeValue,
 		})
 
-		autogold.ExpectFile(t, testOutput{
+		autogold.ExpectFile(t, diffTestOutput{
 			initialValue: initialValue,
 			changeValue:  changeValue,
 			tfOut:        diff.TFOut,
@@ -1705,7 +1705,7 @@ func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 			Config2:  changeValue,
 		})
 
-		autogold.ExpectFile(t, testOutput{
+		autogold.ExpectFile(t, diffTestOutput{
 			initialValue: initialValue,
 			changeValue:  changeValue,
 			tfOut:        diff.TFOut,
@@ -1724,7 +1724,118 @@ func TestDetailedDiffReplacementComputedProperty(t *testing.T) {
 			Config2:  changeValue,
 		})
 
-		autogold.ExpectFile(t, testOutput{
+		autogold.ExpectFile(t, diffTestOutput{
+			initialValue: initialValue,
+			changeValue:  changeValue,
+			tfOut:        diff.TFOut,
+			pulumiOut:    diff.PulumiOut,
+			detailedDiff: diff.PulumiDiff.DetailedDiff,
+		})
+	})
+}
+
+func TestPropertyWithDot(t *testing.T) {
+	t.Parallel()
+	// TODO[pulumi/pulumi-terraform-bridge#2669]
+	t.Skip("We currently fail to return the correct detailed diff for this case")
+
+	res := &schema.Resource{
+		Schema: map[string]*schema.Schema{
+			"prop": {
+				Type:     schema.TypeList,
+				Optional: true,
+				MaxItems: 1,
+				Elem: &schema.Resource{
+					Schema: map[string]*schema.Schema{
+						"foo": {
+							Type:     schema.TypeString,
+							Optional: true,
+						},
+					},
+				},
+			},
+		},
+	}
+
+	t.Run("unchanged", func(t *testing.T) {
+		t.Parallel()
+		initialValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{"foo.bar": cty.StringVal("baz")}),
+			}),
+		})
+		changeValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{"foo.bar": cty.StringVal("baz")}),
+			}),
+		})
+		diff := runDiffCheck(t, diffTestCase{
+			Resource: res,
+			Config1:  initialValue,
+			Config2:  changeValue,
+		})
+
+		autogold.ExpectFile(t, diffTestOutput{
+			initialValue: initialValue,
+			changeValue:  changeValue,
+			tfOut:        diff.TFOut,
+			pulumiOut:    diff.PulumiOut,
+			detailedDiff: diff.PulumiDiff.DetailedDiff,
+		})
+	})
+
+	t.Run("added", func(t *testing.T) {
+		t.Parallel()
+		initialValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{"foo": cty.StringVal("bar")}),
+			}),
+		})
+		changeValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{
+					"foo":     cty.StringVal("bar"),
+					"foo.bar": cty.StringVal("baz"),
+				}),
+			}),
+		})
+		diff := runDiffCheck(t, diffTestCase{
+			Resource: res,
+			Config1:  initialValue,
+			Config2:  changeValue,
+		})
+
+		autogold.ExpectFile(t, diffTestOutput{
+			initialValue: initialValue,
+			changeValue:  changeValue,
+			tfOut:        diff.TFOut,
+			pulumiOut:    diff.PulumiOut,
+			detailedDiff: diff.PulumiDiff.DetailedDiff,
+		})
+	})
+
+	t.Run("deleted", func(t *testing.T) {
+		t.Parallel()
+		initialValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{
+					"foo":     cty.StringVal("bar"),
+					"foo.bar": cty.StringVal("baz"),
+				}),
+			}),
+		})
+		changeValue := cty.ObjectVal(map[string]cty.Value{
+			"prop": cty.ListVal([]cty.Value{
+				cty.ObjectVal(map[string]cty.Value{"foo": cty.StringVal("bar")}),
+			}),
+		})
+		diff := runDiffCheck(t, diffTestCase{
+			Resource: res,
+			Config1:  initialValue,
+			Config2:  changeValue,
+		})
+
+		autogold.ExpectFile(t, diffTestOutput{
 			initialValue: initialValue,
 			changeValue:  changeValue,
 			tfOut:        diff.TFOut,
diff --git a/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/added.golden b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/added.golden
new file mode 100644
index 0000000000..aab5c5c115
--- /dev/null
+++ b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/added.golden
@@ -0,0 +1,44 @@
+crosstests.diffTestOutput{
+	initialValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{
+			AttrTypes: map[string]cty.Type{"prop": {
+				typeImpl: cty.typeList{ElementTypeT: cty.Type{
+					typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{
+						"foo": {typeImpl: cty.primitiveType{
+							Kind: cty.primitiveTypeKind(83),
+						}},
+					}},
+				}},
+			}},
+		}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{"foo": "bar"}}},
+	},
+	changeValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{"prop": {typeImpl: cty.typeList{
+			ElementTypeT: cty.Type{typeImpl: cty.typeObject{
+				AttrTypes: map[string]cty.Type{
+					"foo": {
+						typeImpl: cty.primitiveType{Kind: cty.primitiveTypeKind(83)},
+					},
+					"foo.bar": {typeImpl: cty.primitiveType{Kind: cty.primitiveTypeKind(83)}},
+				},
+			}},
+		}}}}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{
+			"foo":     "bar",
+			"foo.bar": "baz",
+		}}},
+	},
+	tfOut: `
+No changes. Your infrastructure matches the configuration.
+
+Terraform has compared your real infrastructure against your configuration
+and found no differences, so no changes are needed.
+`,
+	pulumiOut: `Previewing update (test):
+  pulumi:pulumi:Stack: (same)
+    [urn=urn:pulumi:test::project::pulumi:pulumi:Stack::project-test]
+Resources:
+    2 unchanged
+`,
+}
diff --git a/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/deleted.golden b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/deleted.golden
new file mode 100644
index 0000000000..bd3964402f
--- /dev/null
+++ b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/deleted.golden
@@ -0,0 +1,42 @@
+crosstests.diffTestOutput{
+	initialValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{
+			AttrTypes: map[string]cty.Type{"prop": {
+				typeImpl: cty.typeList{ElementTypeT: cty.Type{
+					typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{
+						"foo": {typeImpl: cty.primitiveType{
+							Kind: cty.primitiveTypeKind(83),
+						}},
+						"foo.bar": {typeImpl: cty.primitiveType{Kind: cty.primitiveTypeKind(83)}},
+					}},
+				}},
+			}},
+		}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{
+			"foo":     "bar",
+			"foo.bar": "baz",
+		}}},
+	},
+	changeValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{"prop": {typeImpl: cty.typeList{
+			ElementTypeT: cty.Type{typeImpl: cty.typeObject{
+				AttrTypes: map[string]cty.Type{"foo": {
+					typeImpl: cty.primitiveType{Kind: cty.primitiveTypeKind(83)},
+				}},
+			}},
+		}}}}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{"foo": "bar"}}},
+	},
+	tfOut: `
+No changes. Your infrastructure matches the configuration.
+
+Terraform has compared your real infrastructure against your configuration
+and found no differences, so no changes are needed.
+`,
+	pulumiOut: `Previewing update (test):
+  pulumi:pulumi:Stack: (same)
+    [urn=urn:pulumi:test::project::pulumi:pulumi:Stack::project-test]
+Resources:
+    2 unchanged
+`,
+}
diff --git a/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/unchanged.golden b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/unchanged.golden
new file mode 100644
index 0000000000..be541fbc79
--- /dev/null
+++ b/pkg/internal/tests/cross-tests/testdata/TestPropertyWithDot/unchanged.golden
@@ -0,0 +1,38 @@
+crosstests.diffTestOutput{
+	initialValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{
+			AttrTypes: map[string]cty.Type{"prop": {
+				typeImpl: cty.typeList{ElementTypeT: cty.Type{
+					typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{
+						"foo.bar": {typeImpl: cty.primitiveType{
+							Kind: cty.primitiveTypeKind(83),
+						}},
+					}},
+				}},
+			}},
+		}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{"foo.bar": "baz"}}},
+	},
+	changeValue: cty.Value{
+		ty: cty.Type{typeImpl: cty.typeObject{AttrTypes: map[string]cty.Type{"prop": {typeImpl: cty.typeList{
+			ElementTypeT: cty.Type{typeImpl: cty.typeObject{
+				AttrTypes: map[string]cty.Type{"foo.bar": {
+					typeImpl: cty.primitiveType{Kind: cty.primitiveTypeKind(83)},
+				}},
+			}},
+		}}}}},
+		v: map[string]interface{}{"prop": []interface{}{map[string]interface{}{"foo.bar": "baz"}}},
+	},
+	tfOut: `
+No changes. Your infrastructure matches the configuration.
+
+Terraform has compared your real infrastructure against your configuration
+and found no differences, so no changes are needed.
+`,
+	pulumiOut: `Previewing update (test):
+  pulumi:pulumi:Stack: (same)
+    [urn=urn:pulumi:test::project::pulumi:pulumi:Stack::project-test]
+Resources:
+    2 unchanged
+`,
+}
diff --git a/pkg/tfbridge/diff_test.go b/pkg/tfbridge/diff_test.go
index 5cba5ec1b1..782dd78819 100644
--- a/pkg/tfbridge/diff_test.go
+++ b/pkg/tfbridge/diff_test.go
@@ -2173,6 +2173,7 @@ type diffTestCase struct {
 }
 
 func diffTest2(t *testing.T, tc diffTestCase) {
+	t.Helper()
 	ctx := context.Background()
 	res := &v2Schema.Resource{
 		Schema: tc.resourceSchema,
@@ -2275,3 +2276,42 @@ func TestChangingMaxItems1FilterProperty(t *testing.T) {
 		},
 	})
 }
+
+func TestPropertyWithDot(t *testing.T) {
+	t.Parallel()
+	// TODO[pulumi/pulumi-terraform-bridge#2669]
+	t.Skip("We currently fail to return the correct detailed diff for this case")
+
+	schema := map[string]*v2Schema.Schema{
+		"prop": {
+			Type:     v2Schema.TypeMap,
+			Optional: true,
+			Elem: &v2Schema.Schema{
+				Type: v2Schema.TypeString,
+			},
+		},
+	}
+
+	diffTest2(t, diffTestCase{
+		resourceSchema: schema,
+		state: resource.PropertyMap{
+			"prop": resource.NewObjectProperty(resource.PropertyMap{
+				"foo": resource.NewStringProperty("bar"),
+			}),
+		},
+		inputs: resource.PropertyMap{
+			"prop": resource.NewObjectProperty(resource.PropertyMap{
+				"foo.bar": resource.NewStringProperty("baz"),
+			}),
+		},
+		expectedDiffChanges: pulumirpc.DiffResponse_DIFF_SOME,
+		expected: map[string]*pulumirpc.PropertyDiff{
+			"prop.foo": {
+				Kind: pulumirpc.PropertyDiff_DELETE,
+			},
+			"prop[\"foo.bar\"]": {
+				Kind: pulumirpc.PropertyDiff_ADD,
+			},
+		},
+	})
+}