Since this functionality has 'eluded' iOS for years I figured I would make a guide on how to use a stock iPhone to email multiple attachments or reply to an email with attachments. Now while this is not the most eloquent way ever... it's currently the only way possible that I know of on an iOS device. So the problem begins with how on the iPhone most of the time if you try to attach a file the only two options you are given are photos or videos. I'm going to show you below how you can attach ANY type of file (doc, spreadsheet, ppt, pdf, voice memo, mp4, etc) to an email on your iPhone. NOTE: iPad users can use Safari and skip the below steps 1, 2 and 5 (iPhone users need a different browser than Safari). Step 1: Download a browser that let's you set the 'user agent'. By this I mean how in a browser like iCab (my personal recommendation) you can go under settings and switch the user agent so that a website thinks you are using a firefox, internet explorer, or other non-mobile browser. Step 2: Set the user agent to a desktop type browser. Now this won't always work on the first try. Sometimes you have to try each one until you find one that works. On iCab I use 'internet explorer 10' user agent. Step 3: Log into your gmail account Step 4: Click the 'desktop' button at the bottom Step 5: Click the 'gmail view: standard' button at the bottom (This step is why if you are using an iPhone you need a browser that you can set the user agent. If you are using Safari and press this button it will force you back to the mobile iPhone view of Gmail) Step 6: Now that you are in the real desktop version of Gmail, you can compose a new brand new email or reply to an email Step 7: Click the paperclip file attachment icon located at the bottom of the email you are typing in. Step 8: Click the Google drive triangle icon next to the paperclip. Step 9: Click 'My Drive' Step 10: Double click whichever files you want to attach. Single clicking a file won't select it. You can tell once there is a check mark on the files you want to attach. At this point you can attach as many as you want. Step 11: Click the blue insert button Step 12: Hit send! Now the only trick left is finding applications which allow you to upload files from your iPhone to Google Drive (which there are TONS on the app store). Almost any worthy files app will have this ability built right into the app. If you are confused about this simply let me know and I will give some examples of apps that let you do uploads of various files to Google Drive. Now, I can already hear the ungrateful moaning in advance: "But but but... (insert any of the below) - There's too many steps involved" - Android is soooooo much easier" - I don't want to use Google Drive" - Why doesn't Apple make this easier" For those people, I can't help you. Either don't use this method or go with another smartphone OS. This trick is simply for those who are grateful to have the capability on an iPhone (or iPad) in a pinch. For those who actually find this feature helpful, I'm glad it helps plug up an annoying gap of iOS. Once you get the hang of this it becomes very easy and only a few clicks. Cheers!