diff --git a/pkg/test_runner/lib/src/update_errors.dart b/pkg/test_runner/lib/src/update_errors.dart
index f8068c4b1ac2..e7c1463d3b65 100644
--- a/pkg/test_runner/lib/src/update_errors.dart
+++ b/pkg/test_runner/lib/src/update_errors.dart
@@ -105,13 +105,15 @@ String updateErrorExpectations(
     var previousLength = -1;
 
     for (var error in errorsHere) {
-      // Try to indent the line nicely to match either the existing expectation
-      // that is being regenerated, or, barring that, the previous line of code.
-      var indent = indentation[i + 1] ?? previousIndent;
+      // Try to indent the line nicely to match the existing expectation that
+      // is being regenerated. If that collides with the carets, then indent
+      // the line based on the preceding line of code. If the caret still
+      // doesn't fit with that indentation, we'll use an explicit location.
+      var indent = indentation[i + 1];
+      if (indent == null || error.column - 1 < indent + 2) {
+        indent = previousIndent;
+      }
 
-      // If the error is to the left of the indent and the "//", sacrifice the
-      // indentation.
-      if (error.column - 1 < indent + 2) indent = 0;
       var comment = "${" " * indent}//";
 
       // Write the location line, unless we already have an identical one. Allow
@@ -120,12 +122,11 @@ String updateErrorExpectations(
           (previousLength != 0 &&
               error.length != 0 &&
               error.length != previousLength)) {
-        // If the error can't fit in a line comment, or no source location is
-        // specified, use an explicit location.
-        if (error.column <= 2) {
+        // If the error location starts to the left of the line comment, or no
+        // error length is specified, use an explicit location.
+        if (error.column - 1 < indent + 2) {
           if (error.length == 0) {
-            result.add("$comment [error column "
-                "${error.column}]");
+            result.add("$comment [error column ${error.column}]");
           } else {
             result.add("$comment [error column "
                 "${error.column}, length ${error.length}]");
diff --git a/pkg/test_runner/test/update_errors_test.dart b/pkg/test_runner/test/update_errors_test.dart
index 9477be9fc4c8..953128d04ccd 100644
--- a/pkg/test_runner/test/update_errors_test.dart
+++ b/pkg/test_runner/test/update_errors_test.dart
@@ -229,54 +229,46 @@ main() {
 }
 """);
 
-  // Discards indentation if it would collide with carets.
+  // Discards previous error indentation if it would collide with carets.
   expectUpdate("""
+// This fits:
 int i = "bad";
-        /\/    ^^
-        /\/ [analyzer] previous.error
+      /\/    ^^
+      /\/ [analyzer] previous.error
 
-main() {
-  int i =
-  "bad";
-}
+// This does not:
+int j = "bad";
+       /\/    ^^
+       /\/ [analyzer] previous.error
 """, errors: [
-    makeError(line: 1, column: 9, length: 5, cfeError: "Error."),
-    makeError(line: 7, column: 3, length: 5, analyzerError: "new.error"),
+    makeError(line: 2, column: 9, length: 5, cfeError: "Error."),
+    makeError(line: 7, column: 9, length: 5, cfeError: "Error."),
   ], expected: """
+// This fits:
 int i = "bad";
+      /\/^^^^^
+      /\/ [cfe] Error.
+
+// This does not:
+int j = "bad";
 /\/      ^^^^^
 /\/ [cfe] Error.
-
-main() {
-  int i =
-  "bad";
-/\/^^^^^
-/\/ [analyzer] new.error
-}
 """);
 
-  // Uses an explicit error location if there's no room for the carets.
+  // Uses explicit location if indenting based on preceding code would collide
+  // with carets.
   expectUpdate("""
-int i =
-"bad";
-    /\/    ^^
-    /\/ [analyzer] previous.error
-
-int j =
-"bad";
+main() {
+  ["bad"];
+}
 """, errors: [
-    makeError(line: 2, column: 1, length: 5, analyzerError: "updated.error"),
-    makeError(line: 7, column: 1, length: 5, cfeError: "Error."),
+    makeError(line: 2, column: 4, length: 5, cfeError: "Error."),
   ], expected: """
-int i =
-"bad";
-/\/ [error column 1, length 5]
-/\/ [analyzer] updated.error
-
-int j =
-"bad";
-/\/ [error column 1, length 5]
-/\/ [cfe] Error.
+main() {
+  ["bad"];
+  /\/ [error column 4, length 5]
+  /\/ [cfe] Error.
+}
 """);
 
   // Uses length one if there's no length.