diff --git a/src/extension.ts b/src/extension.ts
index 5ed42f0f..602c89c1 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -27,6 +27,10 @@ export const incLangId = "objectscript-macros";
 export const cspLangId = "objectscript-csp";
 export const outputLangId = "vscode-objectscript-output";
 
+const dotPrefixRegex = /^(\s*(?:\.\s*)+)/;
+const dotIndentLanguages = new Set<string>([macLangId, intLangId]);
+const dotIndentSkipDocuments = new Set<string>();
+
 import * as url from "url";
 import path = require("path");
 import {
@@ -1050,6 +1054,72 @@ export async function activate(context: vscode.ExtensionContext): Promise<any> {
     }
   }
 
+  context.subscriptions.push(
+    vscode.workspace.onDidChangeTextDocument(async (event) => {
+      if (!dotIndentLanguages.has(event.document.languageId)) {
+        return;
+      }
+
+      const docUriString = event.document.uri.toString();
+      if (dotIndentSkipDocuments.has(docUriString)) {
+        return;
+      }
+
+      const editor = vscode.window.visibleTextEditors.find((e) => e.document === event.document);
+      if (!editor) {
+        return;
+      }
+
+      for (const change of event.contentChanges) {
+        if (!change.text.includes("\n")) {
+          continue;
+        }
+
+        const newLineNumber = change.range.start.line + 1;
+        if (newLineNumber >= event.document.lineCount || newLineNumber <= 0) {
+          continue;
+        }
+
+        const previousLine = event.document.lineAt(newLineNumber - 1).text;
+        const prefixMatch = previousLine.match(dotPrefixRegex);
+        if (!prefixMatch) {
+          continue;
+        }
+
+        let insertText = prefixMatch[1];
+        if (!insertText.endsWith(" ")) {
+          insertText += " ";
+        }
+
+        const remainder = previousLine.slice(prefixMatch[1].length);
+        if (remainder.startsWith(";")) {
+          insertText += ";";
+        }
+
+        const newLine = event.document.lineAt(newLineNumber);
+        if (newLine.text.startsWith(insertText)) {
+          continue;
+        }
+
+        const indentMatch = newLine.text.match(/^\s*/);
+        const indentLength = indentMatch ? indentMatch[0].length : 0;
+        const replaceRange = new vscode.Range(newLine.range.start, new vscode.Position(newLineNumber, indentLength));
+
+        dotIndentSkipDocuments.add(docUriString);
+        try {
+          await editor.edit(
+            (editBuilder) => {
+              editBuilder.replace(replaceRange, insertText);
+            },
+            { undoStopBefore: false, undoStopAfter: false }
+          );
+        } finally {
+          dotIndentSkipDocuments.delete(docUriString);
+        }
+      }
+    })
+  );
+
   openedClasses = workspaceState.get("openedClasses") ?? [];
 
   /** The stringified URIs of all `isfs` documents that are currently open in a UI tab */
diff --git a/src/test/suite/extension.test.ts b/src/test/suite/extension.test.ts
index d2cdb1a9..3f4ba604 100644
--- a/src/test/suite/extension.test.ts
+++ b/src/test/suite/extension.test.ts
@@ -21,6 +21,17 @@ async function waitForIndexedDocument(documentName: string, workspaceFolderName:
   assert.fail(`Timed out waiting for '${documentName}' to be indexed in workspace folder '${workspaceFolderName}'.`);
 }
 
+async function waitForCondition(predicate: () => boolean, timeoutMs = 1000, message?: string): Promise<void> {
+  const start = Date.now();
+  while (Date.now() - start < timeoutMs) {
+    if (predicate()) {
+      return;
+    }
+    await new Promise((resolve) => setTimeout(resolve, 10));
+  }
+  assert.fail(message ?? "Timed out waiting for condition");
+}
+
 function getDefinitionTargets(definitions: (vscode.Location | vscode.DefinitionLink)[]): vscode.Uri[] {
   return definitions
     .map((definition) => ("targetUri" in definition ? definition.targetUri : definition.uri))
@@ -44,6 +55,42 @@ suite("Extension Test Suite", () => {
     assert.ok("All good");
   });
 
+  test("Dot-prefixed statements continue on newline", async () => {
+    const document = await vscode.workspace.openTextDocument({
+      language: "objectscript",
+      content: "    . Do ##class(Test).Run()",
+    });
+    const editor = await vscode.window.showTextDocument(document);
+    try {
+      await editor.edit((editBuilder) => {
+        editBuilder.insert(document.lineAt(0).range.end, "\n");
+      });
+      await waitForCondition(() => document.lineCount > 1);
+      await waitForCondition(() => document.lineAt(1).text.length > 0);
+      assert.strictEqual(document.lineAt(1).text, "    . ");
+    } finally {
+      await vscode.commands.executeCommand("workbench.action.closeActiveEditor");
+    }
+  });
+
+  test("Dot-prefixed semicolon comments continue on newline", async () => {
+    const document = await vscode.workspace.openTextDocument({
+      language: "objectscript",
+      content: "  . ; Comment",
+    });
+    const editor = await vscode.window.showTextDocument(document);
+    try {
+      await editor.edit((editBuilder) => {
+        editBuilder.insert(document.lineAt(0).range.end, "\n");
+      });
+      await waitForCondition(() => document.lineCount > 1);
+      await waitForCondition(() => document.lineAt(1).text.length > 0);
+      assert.strictEqual(document.lineAt(1).text, "  . ;");
+    } finally {
+      await vscode.commands.executeCommand("workbench.action.closeActiveEditor");
+    }
+  });
+
   test("Go to Definition resolves to sibling workspace folder", async function () {
     this.timeout(10000);
     await waitForIndexedDocument("MultiRoot.Shared.cls", "shared");