Last week’s edition, Contact Improv, led me to realize that the same multi-touch gestures are possible in other apps that support organizing items in folders, lists, etc.

However, the most mind-blowing discovery was in response to this question: “How do I attach a bunch of photos to an email I’ve already started composing?”

Mail: Insert Photo or Video

On iPhone, only as of iOS 15 has Mail’s Insert Photo or Video interface permitted attaching to an email message more than one photo or video at a time. You do this by tapping the cursor in the body of a message and choosing Insert Photo or Video from the menu.

The initial interface provided in Mail is limited to a single view of square photo tiles and provides no way to preview an item larger before adding to the message. Only if you tap All Photos can you reach a panel where a long-press previews an image and enables selection. However, doing so selects the single item and returns to the Mail message instead of enabling multi-selection.

A possible workaround to this would be to select an item so it appears in the message and use that as a method of preview, deselecting if you choose not to include it. Doing so is tedious, though, especially when you want to attach something taken earlier than the most recent handful of photos (depending on the size of your phone).

Photos: Select & Copy

A completely different approach is to select pictures and videos in Photos directly, instead of via Mail. Photos enables zooming in and out for easier discernment in the tile view. (There are five levels of zoom.)

It’s notable that in versions prior to iOS 15, Photos’ share sheet would only allow sharing up to five items to the Mail app. Also, using the share sheet this way generates a new email message and cannot make use of an existing draft.

For the one-tap-at-a-time method, tap Select and tap the multiple items you want to attach to the email. Then, tap the Share button () and choose Copy Photos. Or, tap the  and choose Copy. Switch to Mail, tap or long press the cursor, and Paste.

Drag & Drop From Photos to Mail

Alternatively, check out this cool approach: In iOS 15 or later, in Photos, long press and drag one item. While holding it, tap additional items, scrolling or navigating as needed to reach them.

For example, you can select items located in different albums. When done, switch to Mail and drop them in the drafted message. No need to use the menu at all.

In the screenshot above, I switch directly to Mail, the most recent app, by swiping the Home bar at the bottom from left to right.

When emailing a large number of photos and/or videos, it’s important to note that many email servers limit message size, often with a 20MB max. Therefore, I recommend using Mail Drop, if prompted.

This feature uploads large attachments to your iCloud account and provides a download link to recipients who don’t use Apple Mail. (Mail downloads these attachments automatically.)

The same drag-and-drop method described here works in apps like Mail and Notes where you can organize items in folders, or to put pictures and videos in albums using Photos.

However, the workflow described above is extraordinary because it involves taking content out of Photos and using it in another app.