Outlook & Microsoft 365 Integration

Deal Run sends deal marketing emails from your own email address for deliverability and trust (see Connecting Your Email Account for the rationale). Most of our users are on Gmail, but a meaningful chunk — usually bigger teams and long-time investors — live in Outlook or Microsoft 365. This page covers how to use your Outlook inbox alongside Deal Run until full Microsoft Graph integration ships.

Current status: manual workflow, Microsoft Graph on the roadmap

Deal Run has a first-class Gmail API integration (one-click connect from Account > Email Integration). Microsoft Graph — the equivalent API for Outlook and Microsoft 365 — is on the roadmap but not yet live. Until it ships, Outlook users can still send deal blast emails, just through a manual copy-paste workflow instead of an automated one.

Step 1: Set Outlook as your reply-to in Deal Run

1. Go to Account > Dispo Profile in Deal Run.
2. Enter your Outlook address (e.g., john@yourcompany.com or jdoe@outlook.com) in the Email field.
3. Click outside the field to save.

Now any marketing page contact form, PDF deal package, and auto-generated message drafts will show your Outlook address as the reply-to. When investors hit reply on your deal marketing emails, their response lands in your Outlook inbox.

Step 2: One-at-a-time emails (from your phone)

For warm, personal outreach — the kind that actually gets replies — email one investor at a time from your phone:

1. Open the Deal Run mobile app and navigate to Sell > Outreach on a deal.
2. Tap Email on an investor card. Deal Run composes a draft (AI-written subject + body + your marketing page link) and opens it via mailto:.
3. iOS or Android hands the draft to Outlook (as long as Outlook is installed and signed in). Review, adjust if needed, send.
4. Back in Deal Run, tap Log Interaction to mark Sent.

If mailto: links open the built-in iOS Mail or Gmail instead of Outlook: iOS > Settings > Apps > Mail > Default Mail App > Outlook. Android: Settings > Apps > Default apps > Email app > Outlook.

Step 3: Bulk blasts (from a laptop)

For a deal blast to 50+ buyers at once, switch to a laptop. Phone email clients don't handle long BCC lists or HTML formatting well.

1. Open a deal on your laptop and go to Sell > Market.
2. Make sure your marketing package is published. Copy the public URL (dealrun.ai/p/[slug]).
3. Click the Email Blast section. Deal Run generates a branded HTML email with your property photo, specs, pricing, and a call-to-action button linking to your marketing page.
4. Click Copy HTML (or Copy Plain Text if you prefer — plain text has better deliverability on cold lists).
5. Open Outlook on the web or in the desktop app. Compose a new message. Paste. Outlook will render the HTML properly.
6. Add your buyer list recipients to the BCC field (never CC — BCC keeps every recipient private and makes each email look personal).
7. Send.

Step 4: Exporting your buyer list for Outlook

Outlook won't let you paste 50 email addresses directly into a BCC field reliably — after about 20 it starts reformatting things. Better approach:

1. In Deal Run, go to Buyers (your CRM).
2. Filter by territory or tag to get the segment you want to email.
3. Click Export CSV.
4. Open the CSV, copy the email column, and paste into Outlook's BCC field. Outlook will recognize the semicolon-separated list and turn each into a proper recipient.

If you're on Microsoft 365, you can also import the CSV as an Outlook Contact Group: People > New Contact Group > Add Members > From Outlook Contacts after importing. That way you can reuse the list for multiple blasts without re-pasting.

Step 5: Outlook sending limits

Outlook enforces stricter limits than Gmail:

• Outlook.com (free Outlook): 500 emails per day, 100 recipients per message
• Microsoft 365 Business: 10,000 emails per day, 500 recipients per message
• Microsoft 365 Enterprise: Same 10,000/day, 500/message limit — Microsoft does not sell "unlimited sending" at any tier

For typical wholesale blasts (100–500 buyers) the Microsoft 365 Business tier is more than enough. If you're on free Outlook.com and you regularly hit the 500/day limit, that's the upgrade signal.

Step 6: Capturing replies in Deal Run

Without Microsoft Graph integration, Outlook replies don't automatically appear in Deal Run's communication log. Two options:

• Manual logging (fast). When an interesting reply comes in, copy the sender name and the first couple of lines into Deal Run's outreach page: find the investor in the queue, click Log Interaction, paste into notes.
• Outlook forwarding rule (automatic, partial). Set up an Outlook rule: if the subject line contains your deal's D-number, forward to deals@yourdomain.com. Then in Deal Run's Zapier integration, set up a zap that reads forwarded emails and logs them to the right deal. This takes about 20 minutes to set up but runs on autopilot after that.

When Microsoft Graph integration ships

The planned flow is identical to the Gmail API integration: click Connect Outlook, complete the Microsoft OAuth consent screen, and from then on Deal Run composes and sends emails through your Outlook account on your behalf. Replies automatically sync into Deal Run's communication log.

If you want to be notified when Microsoft Graph integration ships, email adam@dealrun.ai with the subject "Outlook waitlist" — we'll prioritize it based on demand.

Troubleshooting

Outlook strips the HTML formatting from my pasted email

This happens when you paste into Outlook's "plain text" composer. Switch to rich text: Message > Format Text > HTML. Then paste again.

My Outlook emails go to spam

Microsoft 365 domains have strong reputation, but cold-list blasting to any email provider can trip spam filters. Fixes: (1) warm the list by sending small batches first, (2) always include unsubscribe text and a plain-text version, (3) avoid excessive links — one CTA button to your marketing page is enough.

Recipients say the email didn't arrive but Outlook shows it as sent

Microsoft's "Sent" status means it left your outbox, not that it was delivered. Check Microsoft 365 admin center > Mail flow > Message trace for delivery status. If you're on free Outlook.com, you don't get message trace — use a test send to a personal address on Gmail and iCloud to spot-check deliverability.

Related guides

• Connecting Gmail (first-class integration)
• Apple Mail integration
• Sending your first email blast
• Tracking delivery, opens, and clicks