diff --git a/cli/tools/lint/linter.rs b/cli/tools/lint/linter.rs
index 3b6e8c68f4..5c71472322 100644
--- a/cli/tools/lint/linter.rs
+++ b/cli/tools/lint/linter.rs
@@ -197,7 +197,7 @@ impl CliLinter {
         media_type,
         &self.linter,
         self.deno_lint_config.clone(),
-        source.text_info_lazy(),
+        &source,
         &diagnostics,
         &external_linter_container,
       )?;
@@ -215,7 +215,7 @@ impl CliLinter {
         log::warn!(
           concat!(
             "Reached maximum number of fix iterations for '{}'. There's ",
-            "probably a bug in Deno. Please fix this file manually.",
+            "probably a bug in the lint rule. Please fix this file manually.",
           ),
           specifier,
         );
@@ -243,25 +243,75 @@ fn apply_lint_fixes_and_relint(
   media_type: MediaType,
   linter: &DenoLintLinter,
   config: DenoLintConfig,
-  text_info: &SourceTextInfo,
+  original_source: &ParsedSource,
   diagnostics: &[LintDiagnostic],
   external_linter_container: &ExternalLinterContainer,
 ) -> Result<Option<(ParsedSource, Vec<LintDiagnostic>)>, AnyError> {
+  let text_info = original_source.text_info_lazy();
   let Some(new_text) = apply_lint_fixes(text_info, diagnostics) else {
     return Ok(None);
   };
 
-  let (source, diagnostics) = linter
-    .lint_file(LintFileOptions {
+  let lint_with_text = |new_text: String| {
+    let (source, diagnostics) = linter.lint_file(LintFileOptions {
       specifier: specifier.clone(),
       source_code: new_text,
       media_type,
-      config,
+      config: config.clone(),
       external_linter: external_linter_container.get_callback(),
-    })
-    .context(
-      "An applied lint fix caused a syntax error. Please report this bug.",
-    )?;
+    })?;
+    let mut new_diagnostics = source.diagnostics().clone();
+    new_diagnostics.retain(|d| !original_source.diagnostics().contains(d));
+    if let Some(diagnostic) = new_diagnostics.pop() {
+      return Err(AnyError::from(diagnostic));
+    }
+    Ok((source, diagnostics))
+  };
+
+  let (source, diagnostics) = match lint_with_text(new_text) {
+    Ok(result) => result,
+    Err(err) => {
+      let utf16_map = Utf16Map::new(text_info.text_str());
+      // figure out which diagnostic caused a syntax error
+      let mut diagnostics = diagnostics.to_vec();
+      while let Some(last_diagnostic) = diagnostics.pop() {
+        let Some(lint_fix) = last_diagnostic.details.fixes.first() else {
+          continue;
+        };
+        let success = match apply_lint_fixes(text_info, &diagnostics) {
+          Some(new_text) => lint_with_text(new_text).is_ok(),
+          None => true,
+        };
+        if success {
+          let mut changes_text = String::new();
+          for change in &lint_fix.changes {
+            let utf8_start =
+              (change.range.start - text_info.range().start) as u32;
+            let utf8_end = (change.range.end - text_info.range().start) as u32;
+            let utf16_start = utf16_map
+              .utf8_to_utf16_offset(utf8_start.into())
+              .unwrap_or(utf8_start.into());
+            let utf16_end = utf16_map
+              .utf8_to_utf16_offset(utf8_end.into())
+              .unwrap_or(utf8_end.into());
+            changes_text.push_str(&format!(
+              "Range: [{}, {}]\n",
+              u32::from(utf16_start),
+              u32::from(utf16_end)
+            ));
+            changes_text.push_str(&format!("Text: {:?}\n\n", &change.new_text));
+          }
+          return Err(err).context(format!(
+            "The '{}' rule caused a syntax error applying '{}'.\n\n{}",
+            last_diagnostic.details.code, lint_fix.description, changes_text
+          ));
+        }
+      }
+      return Err(err).context(
+        "A lint fix caused a syntax error. This is a bug in a lint rule.",
+      );
+    }
+  };
 
   if let Some(err) = external_linter_container.take_error() {
     return Err(err);
diff --git a/cli/tools/lint/reporters.rs b/cli/tools/lint/reporters.rs
index 447086a0d2..2aa50b6de8 100644
--- a/cli/tools/lint/reporters.rs
+++ b/cli/tools/lint/reporters.rs
@@ -55,11 +55,19 @@ impl LintReporter for PrettyLintReporter {
 
   fn visit_error(&mut self, file_path: &str, err: &AnyError) {
     log::error!("Error linting: {file_path}");
-    if let Some(CoreError::Js(js_error)) = err.downcast_ref::<CoreError>() {
-      log::error!("   {}", format_js_error(js_error));
-      return;
+    let text =
+      if let Some(CoreError::Js(js_error)) = err.downcast_ref::<CoreError>() {
+        format_js_error(js_error)
+      } else {
+        format!("{err:#}")
+      };
+    for line in text.split('\n') {
+      if line.is_empty() {
+        log::error!("");
+      } else {
+        log::error!("    {}", line);
+      }
     }
-    log::error!("   {err}");
   }
 
   fn close(&mut self, check_count: usize) {
diff --git a/tests/specs/lint/lint_plugin_fix_error/__test__.jsonc b/tests/specs/lint/lint_plugin_fix_error/__test__.jsonc
new file mode 100644
index 0000000000..57da106ff6
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_fix_error/__test__.jsonc
@@ -0,0 +1,6 @@
+{
+  "tempDir": true,
+  "args": "lint --fix",
+  "output": "fix.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/lint/lint_plugin_fix_error/deno.json b/tests/specs/lint/lint_plugin_fix_error/deno.json
new file mode 100644
index 0000000000..57b9dcb364
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_fix_error/deno.json
@@ -0,0 +1,5 @@
+{
+  "lint": {
+    "plugins": ["./plugin.ts"]
+  }
+}
diff --git a/tests/specs/lint/lint_plugin_fix_error/fix.out b/tests/specs/lint/lint_plugin_fix_error/fix.out
new file mode 100644
index 0000000000..aed9d4df8a
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_fix_error/fix.out
@@ -0,0 +1,11 @@
+Error linting: [WILDLINE]main.ts
+    The 'test-plugin/my-rule' rule caused a syntax error applying 'Fix this test-plugin/my-rule problem'.
+
+    Range: [14, 18]
+    Text: "garbage test test"
+
+    : Expected a semicolon at file:///[WILDLINE]/main.ts:1:23
+
+      const value = garbage test test;
+                            ~~~~
+Checked 2 files
diff --git a/tests/specs/lint/lint_plugin_fix_error/main.ts b/tests/specs/lint/lint_plugin_fix_error/main.ts
new file mode 100644
index 0000000000..5a277eecbb
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_fix_error/main.ts
@@ -0,0 +1,2 @@
+const value = "𝄞";
+console.log(value);
diff --git a/tests/specs/lint/lint_plugin_fix_error/plugin.ts b/tests/specs/lint/lint_plugin_fix_error/plugin.ts
new file mode 100644
index 0000000000..3df9f8655d
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_fix_error/plugin.ts
@@ -0,0 +1,20 @@
+export default {
+  name: "test-plugin",
+  rules: {
+    "my-rule": {
+      create(context) {
+        return {
+          VariableDeclarator(node) {
+            context.report({
+              node: node.init,
+              message: 'should be equal to string "1"',
+              fix(fixer) {
+                return fixer.replaceText(node.init, "garbage test test");
+              },
+            });
+          },
+        };
+      },
+    },
+  },
+};
diff --git a/tests/specs/lint/lint_plugin_infinite_edits/__test__.jsonc b/tests/specs/lint/lint_plugin_infinite_edits/__test__.jsonc
new file mode 100644
index 0000000000..57da106ff6
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_infinite_edits/__test__.jsonc
@@ -0,0 +1,6 @@
+{
+  "tempDir": true,
+  "args": "lint --fix",
+  "output": "fix.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/lint/lint_plugin_infinite_edits/deno.json b/tests/specs/lint/lint_plugin_infinite_edits/deno.json
new file mode 100644
index 0000000000..57b9dcb364
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_infinite_edits/deno.json
@@ -0,0 +1,5 @@
+{
+  "lint": {
+    "plugins": ["./plugin.ts"]
+  }
+}
diff --git a/tests/specs/lint/lint_plugin_infinite_edits/fix.out b/tests/specs/lint/lint_plugin_infinite_edits/fix.out
new file mode 100644
index 0000000000..4dde757781
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_infinite_edits/fix.out
@@ -0,0 +1,12 @@
+Reached maximum number of fix iterations for 'file:///[WILDLINE]/main.ts'. There's probably a bug in the lint rule. Please fix this file manually.
+error[test-plugin/my-rule]: should be equal to string "1"
+ --> [WILDLINE]main.ts:1:15
+  | 
+1 | const value = [WILDLINE];
+  |               [WILDLINE]
+
+  docs: https://docs.deno.com/lint/rules/test-plugin/my-rule
+
+
+Found 1 problem (1 fixable via --fix)
+Checked 2 files
diff --git a/tests/specs/lint/lint_plugin_infinite_edits/main.ts b/tests/specs/lint/lint_plugin_infinite_edits/main.ts
new file mode 100644
index 0000000000..5a277eecbb
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_infinite_edits/main.ts
@@ -0,0 +1,2 @@
+const value = "𝄞";
+console.log(value);
diff --git a/tests/specs/lint/lint_plugin_infinite_edits/plugin.ts b/tests/specs/lint/lint_plugin_infinite_edits/plugin.ts
new file mode 100644
index 0000000000..5926fb868c
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_infinite_edits/plugin.ts
@@ -0,0 +1,20 @@
+export default {
+  name: "test-plugin",
+  rules: {
+    "my-rule": {
+      create(context) {
+        return {
+          VariableDeclarator(node) {
+            context.report({
+              node: node.init,
+              message: 'should be equal to string "1"',
+              fix(fixer) {
+                return fixer.replaceText(node.init, Date.now().toString());
+              },
+            });
+          },
+        };
+      },
+    },
+  },
+};
diff --git a/tests/specs/lint/lint_plugin_utf16/__test__.jsonc b/tests/specs/lint/lint_plugin_utf16/__test__.jsonc
new file mode 100644
index 0000000000..e04db0eaf0
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/__test__.jsonc
@@ -0,0 +1,22 @@
+{
+  "tests": {
+    "lint": {
+      "args": "lint",
+      "output": "lint.out",
+      "exitCode": 1
+    },
+    "fix": {
+      "tempDir": true,
+      "steps": [{
+        "args": "lint --fix",
+        "output": "fix.out"
+      }, {
+        "args": [
+          "eval",
+          "console.log(Deno.readTextFileSync('main.ts').trim())"
+        ],
+        "output": "fixed.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/lint/lint_plugin_utf16/deno.json b/tests/specs/lint/lint_plugin_utf16/deno.json
new file mode 100644
index 0000000000..57b9dcb364
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/deno.json
@@ -0,0 +1,5 @@
+{
+  "lint": {
+    "plugins": ["./plugin.ts"]
+  }
+}
diff --git a/tests/specs/lint/lint_plugin_utf16/fix.out b/tests/specs/lint/lint_plugin_utf16/fix.out
new file mode 100644
index 0000000000..158c556c29
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/fix.out
@@ -0,0 +1 @@
+Checked 2 files
diff --git a/tests/specs/lint/lint_plugin_utf16/fixed.out b/tests/specs/lint/lint_plugin_utf16/fixed.out
new file mode 100644
index 0000000000..46538595af
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/fixed.out
@@ -0,0 +1,2 @@
+const value = "1";
+console.log(value);
diff --git a/tests/specs/lint/lint_plugin_utf16/lint.out b/tests/specs/lint/lint_plugin_utf16/lint.out
new file mode 100644
index 0000000000..cf78dcf9f3
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/lint.out
@@ -0,0 +1,11 @@
+error[test-plugin/my-rule]: should be equal to string "1"
+ --> [WILDLINE]main.ts:1:15
+  | 
+1 | const value = "𝄞";
+  |               ^^^
+
+  docs: https://docs.deno.com/lint/rules/test-plugin/my-rule
+
+
+Found 1 problem (1 fixable via --fix)
+Checked 2 files
diff --git a/tests/specs/lint/lint_plugin_utf16/main.ts b/tests/specs/lint/lint_plugin_utf16/main.ts
new file mode 100644
index 0000000000..5a277eecbb
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/main.ts
@@ -0,0 +1,2 @@
+const value = "𝄞";
+console.log(value);
diff --git a/tests/specs/lint/lint_plugin_utf16/plugin.ts b/tests/specs/lint/lint_plugin_utf16/plugin.ts
new file mode 100644
index 0000000000..40894f5e0e
--- /dev/null
+++ b/tests/specs/lint/lint_plugin_utf16/plugin.ts
@@ -0,0 +1,22 @@
+export default {
+  name: "test-plugin",
+  rules: {
+    "my-rule": {
+      create(context) {
+        return {
+          VariableDeclarator(node) {
+            if (node.init.type !== "Literal" || node.init.value !== "1") {
+              context.report({
+                node: node.init,
+                message: 'should be equal to string "1"',
+                fix(fixer) {
+                  return fixer.replaceText(node.init, '"1"');
+                },
+              });
+            }
+          },
+        };
+      },
+    },
+  },
+};