Unable to send photos from iPhone 11 Pro to my Hotmail email.

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Unable to send photos from iPhone 11 Pro to my Hotmail email.

Debbie 0

Unable to send photos from iPhone 11 Pro to my Hotmail email, so that I can send to my laptop. Shows them as unsent emails. I'm unable to see the unsent emails on my iPhone. Was able to send photos prior to installing IOS 26.4.2. And yes, I have restarted my phone. I always update my iPhone regularly and restart it. Was working fine and able to send photos prior to this latest update without any difficulties.

Debbie 0 Reputation points

2026-04-29T22:03:45.54+00:00

I also forgot to add that after updating my iPhone with IOS 26.4.2, my phone is constantly asking me to sign in to my outlook account, which I never had to do before the update. So, this appears to be an issue with the update maybe??

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Debbie 0 Reputation points

2026-04-29T22:03:45.54+00:00

I also forgot to add that after updating my iPhone with IOS 26.4.2, my phone is constantly asking me to sign in to my outlook account, which I never had to do before the update. So, this appears to be an issue with the update maybe??

Answer 1

To resolve my issues, I ended up doing a basic search in Google on how to resolve issues with apple mail on iPhone. After going through all the various steps including resetting my network settings, I was finally able to send photos. I believe resetting the network settings may have been the ultimate fix.

Also, as you suggested, I was able to go to my Outbox and send the unsent photos. Thank you for that suggestion, because I did not think to look under that folder.

Just to let you know...for the following steps, when I go to Account Settings or anywhere in these steps, it does not give me the option to enter my password. I'm not sure why under Mail, it does not give me an option to enter my password for either Hotmail or Gmail. Maybe it was a one-time deal when I added the accounts for the first time.

1 Re-enter your Hotmail password in iPhone Settings

Go to Settings > Mail > Accounts
Tap your Hotmail/Outlook account
Tap Password (or Account Settings) and re-enter your current password, then tap Done
Open the Mail app and try sending a test email again

Thanks so much for your assistance in this matter!

Chloe-V 7,815 Reputation points Microsoft External Staff Moderator

2026-05-05T23:47:49.3933333+00:00

Hi Debbie,

I’m really glad to hear everything is working well now — and thank you so much for sharing what helped, it will definitely be useful for others too! If anything comes up, please don’t hesitate to reach out anytime.

Answer 2

Chloe-V 7,815 Microsoft External Staff Moderator

Hi Debbie,

Welcome to Microsoft Q&A forum.

To scope this down quickly: when you try to email the photos, are you using the built-in iPhone Mail app (Apple Mail) or the Microsoft Outlook app?

Thanks—reply with just that, and I’ll point you to the exact next steps based on the app you’re using.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Debbie 0 Reputation points

2026-04-30T11:53:42.55+00:00

To be honest, I do not know what iPhone Mail App (Apple Mail) is.

The steps I'm using is I select the photo, then hit the Send To icon and select Mail. So, I'm guessing that I'm using Apple mail.
Chloe-V 7,815 Reputation points Microsoft External Staff Moderator

2026-05-04T00:10:33.99+00:00
Hi Debbie,

Thanks for the detail — if you select a photo and tap Send To (Share) > Mail, that means you’re using the built‑in Apple Mail app on the iPhone (the blue “Mail” icon).

Since the sign‑in prompts started right after iOS 26.4.2 and your photo emails show as “unsent”, the most common cause is the Hotmail/Outlook account needing a fresh re‑authentication in iOS settings. Please try this sequence:

1 Re-enter your Hotmail password in iPhone Settings

Go to Settings > Mail > Accounts

Tap your Hotmail/Outlook account

Tap Password (or Account Settings) and re-enter your current password, then tap Done

Open the Mail app and try sending a test email again

2 Check the Outbox and resend the stuck photo email

Open Mail > go back to the Mailboxes list

Tap Outbox

Open the stuck message and tap Send again

If you don’t see Outbox, make sure your Hotmail/Outlook account still has Mail turned ON under Settings > Mail > Accounts.

3 If it still won’t send: remove and add the account back (refreshes the connection)

Settings > Mail > Accounts > select the Hotmail/Outlook account > Delete Account

Then add it back via Add Account > choose Outlook.com (not “Other/IMAP”) and sign in again
Chloe-V 7,815 Reputation points Microsoft External Staff Moderator

2026-05-04T23:43:17.5433333+00:00

Hi Debbie,

If you still have further concerns, please feel free to let us know.

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Unable to send photos from iPhone 11 Pro to my Hotmail email.

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