How to Attach Two Photos: Complete Guide for All Platforms

You found this page because you need to attach two photos somewhere – maybe in an email, a document, or even a social media post. But when I first tried doing this years ago on my old Android phone, I'll admit it was frustrating. Why won't Gmail let me select both pictures at once? Why does Instagram keep deselecting one when I tap the other?

Honestly, attaching two photos should be simple, but every app and device seems to have hidden rules. I once spent 20 minutes trying to attach before/after renovation photos to a client email before realizing Outlook has that tiny checkbox nobody notices. This guide fixes that.

Why Attaching Two Photos Causes Headaches

Let me guess – you selected the first photo, then the second one vanished? Or you attached both but they arrived upside-down? I've been there. The core problem is that:

• Email services limit attachment sizes (Gmail caps at 25MB)
• Mobile apps prioritize single-image workflows
• Cloud services like Google Drive rearrange files unexpectedly

Just last month, my cousin complained her iPhone kept merging two dog photos into a collage when she just wanted them separate in a text. Apple's "helpful" features sometimes aren't.

Platform Breakdown: Where People Struggle Most

Step-by-Step: Exactly How to Attach Two Photos Anywhere

Attaching in Emails (The Right Way)

For attaching two photos in Gmail:

1. Click the paperclip icon OR drag photos directly into the compose window
2. In file explorer, hold Ctrl (Windows) or Command (Mac) while clicking both photos
3. Click "Open" – both should appear as attachments

But here's what most tutorials miss: If files exceed 25MB, Gmail automatically switches to Google Drive links. To force actual attachments:

• Click the drive icon at bottom
• Toggle "Insert as attachment" for each file

On iPhone Mail app:

1. Tap compose > camera icon above keyboard
2. Select "Photo Library"
3. Tap multiple photos (circle checkmarks appear)
4. Important: Scroll down and tap "Use Selected Photos"

I can't count how many times I skipped step 4 and lost everything. Apple's UX isn't intuitive here.

Social Media: Instagram, Facebook, Twitter

When people ask how to attach two photos on Instagram, they usually mean carousel posts:

1. Tap "+" to create new post
2. Tap the stacked squares icon (top right)
3. Select up to 10 photos – order matters here!
4. Edit individually or apply batch filters

But Facebook's desktop version is trickier:

• In "Create Post", click "Photo/Video"
• Hold Ctrl/Command to select multiple files
• Avoid dragging folders – it uploads entire contents!

Personal rant: Twitter still limits you to four images per tweet, but their cropping algorithm butchers compositions. I stopped attaching vertical photos there.

When You Actually Need to Merge Photos First

Sometimes "attach two photos" means combining them into one file. Here's when you'd do this:

• Sending via platforms with single-image limits (e.g., WhatsApp)
• Creating comparison collages (product reviews, makeup transformations)
• Reducing file count for strict submission forms

Best Tools for Merging Photos

Canva’s my daily driver because:

• Drag-and-drop interface just works
• Pre-set ratios for Instagram/Facebook
• No watermarks on free tier (unlike some sketchy apps)

But for raw speed on iPhone, I use PicCollage when traveling. Their auto-layouts save me 10 minutes per post.

Phone-Specific Tricks You Haven't Seen Elsewhere

Android File Managers Matter More Than You Think

Most Android struggles happen because people use gallery apps instead of file managers. To attach two photos in messaging apps:

1. Open Messages > conversation
2. Tap attachment (paperclip icon)
3. Choose "Files" or "File Manager" NOT "Gallery"
4. Navigate to DCIM > Camera folder
5. Long-press one photo > tap others > click checkmark

Samsung users: Your "My Files" app has a cleaner interface for this. Find it in app drawer.

iPhone's Hidden Selection Shortcut

Instead of tapping individual thumbnails:

1. In Photos app, tap "Select" (top right)
2. Drag your finger across both photos (watch them highlight)
3. Tap share icon > choose app/method

This works in Mail, Messages, Slack – anywhere Apple's share sheet appears. Game changer for selecting 5+ photos.

Workarounds for Broken Platforms

Sometimes technology fights back. When standard attachment methods fail:

• Website uploaders crashing: Switch browsers. Chrome handles large uploads better than Safari.
• Email attachments blocked: Use WeTransfer or Firefox Send (free encrypted transfer)
• WhatsApp compressing quality: Send as "Document" instead of "Image" (preserves resolution)

Last month, Dropbox refused my client's event photos. Solution? Created a shared album via Google Photos – no attachments needed.

Advanced Scenarios: Forms, Portfolios, Cloud Storage

Uploading to Job Portals or Application Forms

Systems like LinkedIn or Workday often have clunky interfaces. Critical steps:

1. Prepare photos as single PDF using Adobe Scan or iOS Notes scanner
2. Name files clearly (e.g., "ID_Front.pdf", "ID_Back.pdf")
3. If multiple upload fields exist, attach separately

I once lost a freelance gig because I merged ID documents incorrectly. Don't be me.

Google Drive & Dropbox Sharing

To attach two photos via cloud link:

1. Upload photos to Drive/Dropbox
2. Right-click files > get shareable link
3. Set permissions to "Anyone with link"
4. Paste link in email/message

But here's the kicker: Always test links from another device! I've seen expired permissions ruin deadlines.

FAQ: Your Attachment Questions Answered

Proven Workflows From My Photography Work

Sharing client proofs taught me efficiency. Here's my current system:

• Email batches: Gmail + Drive links (organize in client folders)
• Mobile sharing: Google Photos shared albums (automatic syncing)
• Printed materials: InDesign exports as single PDF (preserves layout)

The real secret? Consistent file naming. "ProjectName_01.jpg" beats "IMG_28392.jpg" every time.

When All Else Fails: Nuclear Options

Someday you'll face a system that rejects every standard method. Try:

• PrintScreen + Paste: Open both photos > Win+Shift+S (Windows) or Cmd+Ctrl+Shift+4 (Mac) to screenshot > paste directly into email body
• Old-school fax apps: Seriously. Fax.Plus lets you "attach" images as fax pages (bypasses email filters)
• Burn to CD: Only half joking. Government agencies still require this for some submissions

I once resorted to mailing a USB drive to a rural client with satellite internet. Do what works.

Final Reality Check

Attaching two photos shouldn’t require a PhD. But between operating systems, apps, and updates, methods change monthly. Bookmark this guide – I update it quarterly as platforms evolve. Got a weird edge case? Email me photos of your error messages. We’ll solve it together.