Outlook Classic vs. New

Summary

New Outlook has begun to appear on campus, even though it's not fully-baked.  This article will define the reasons you may or may not want to use "New" or "Classic".

Feature

Classic Outlook (Windows)

New Outlook (Windows)

Outlook on the Web

Guidance / Notes

Add Email Reminders (Including Custom) Can be added to events created in Classic using New or Web.
Duplicate Events Events created in Classic can be duplicated using New or Web. The duplicated meeting will keep the original meeting's chat history.
.ics Files ⚠️ (won't open when double-clicked, must import) ⚠️ (must import)  

Offline use

⚠️ (partial; improving)

If you travel/work with spotty internet, Classic is safest.

PST files (.pst)

⚠️ (partial)

If you rely on PST archives, Classic is more complete.

Mail merge

⚠️ / No (varies by note)

⚠️

Traditional Word/Excel mail merge works best in Classic.

Quick Parts

🕒 (coming soon)

Use Classic until New catches up.

COM add-ins / VBA

If you depend on legacy add-ins, stay on Classic.

Web add-ins (Office Add-ins)

Modern add-ins are supported across experiences.

Multiple profiles

🕒

If you switch between separate Outlook profiles, use Classic.

Shared mailbox (folders)

Works across endpoints.

Shared mailbox as account (manage rules/categories/OOO)

✅ (rollout-dependent)

Supported in New, availability can vary.

controls improving but inconsistent across tenants

Rules (complex)

⚠️ (partial)

⚠️

Classic tends to offer more for complex rules.

Folder colors

✅ (does not sync to Web)

✅ (does not sync to New)

New/OWA advantage; note one‑way/unsynced behaviors.

Pin messages

New/OWA support pinning.

.EML / .MSG / .OFT handling

✅ for .eml; ⚠️ for .msg/.oft

If you regularly handle .msg files, Classic is more reliable.

Notes module

⚠️ (partial)

If you use Outlook Notes, Classic is safer.

Distribution lists / groups (UX)

🔁 Revised experience

🔁

Experience differs in New; often managed via portal on Web.

Contact lists (basic)

Basic contact lists work across endpoints.

Share a Contacts folder

🕒/⚠️ (investigating)

🕒/⚠️ (investigating)

🕒/⚠️ (investigating)

Microsoft lists as "Investigating".

Copilot features in Outlook

Available where licensed.

Drag calendar item to other calendar

Classic only per internal notes.

Drag email to desktop / Save message file

✅(MSG drag‑drop)

File > Save As (EML)

Different file handling between Classic and New.

"File" menu in Calendar

Classic and Web have a Calendar File menu; New does not.

Forward from Group mailbox

❌(item type invalid)

Forwarding from Group mailbox not available in New (per notes).

Roaming Signatures

Roaming signatures supported in New.

HTML/CSS Rendering If email messages don't appear correctly, use Outlook New or Web.
External content / “Show blocked content” (images) ✅ (global Trust Center control + per‑message download) ❌ (no equivalent global control; Safe Senders / per‑message only) ⚠️ (per‑message + Safe Senders only) Classic allows global enable/disable of blocked content behavior; New/OWA require per-message or Safe Sender trust
Trust Center / advanced client security controls na Trust Center model largely absent in New; controls simplified or removed

NOTES:

  • Classic Outlook remains on the computer, even after a migration to Outlook (new).
  • Both Outlook classic and new can exist and run on a computer at the same time. There’s no conflict.
  • Outlook (classic) for Windows will remain supported until at least 2029.
  • Change to Outlook (new) when YOU are ready, not when Microsoft tries to force you.

Sources