1. mikedaub's Avatar
    I am currently running an iPhone 6 with iOS 8.1 with the mail app set up to use Gmail and multiple aliases. I used this website to set it up [redacted]. I also have the same exact set up running on a 2nd gen iPad, also running 8.1.

    My problem is, I can send mail perfectly fine all day on the iPhone. Every message I send goes through without issue. However, when I try to send a picture (go to photos, share, use mail) it doesn't actually send the message. I hit the send button, and it seems like it does, but nothing. It never appears in the sent bin, in the drafts, or anything like that. I then just open up and log into the Gmail app, and send it that way. So, I know there isn't an issue with the photo, or data service or anything. It has to be with the Mail app. The really odd part is, its just on my iPhone, not on my iPad.

    When I originally set it up, everything worked fine, then just 1 weekend, it no longer sent. I don't think I changed any settings, as I just verified on the iPad and they are all the same.

    I am recently new to iOS, so does anyone have any suggestions on how to get this working. Using the Gmail app is a workaround, but its a pain to have to keep doing it..

    Thanks in advance..

    Sent from my iPad using Tapatalk
    10-27-2014 05:41 PM
  2. Just_Me_D's Avatar
    Try going to Settings - General - Reset and then select "Reset Network Settings" and see if that fixes it for you.
    10-27-2014 05:50 PM
  3. mikedaub's Avatar
    Nope. Sorry. Thanks but that didn't work. However, it did ask me what size to send, which it hasn't for a LONG time.

    Also, after I wrote that post, I tried deleting the account completely, and reentering it, and that didn't help either..
    10-27-2014 05:59 PM
  4. Ledsteplin's Avatar
    Nope. Sorry. Thanks but that didn't work. However, it did ask me what size to send, which it hasn't for a LONG time.

    Also, after I wrote that post, I tried deleting the account completely, and reentering it, and that didn't help either..
    Have you checked the address being sent from. Also, have you tried attaching the photo in the mail app, rather than from Photos?
    Here's How:
    Press on text field.
    Mail app doesn't always send mail with attachment-imageuploadedbytapatalk1414455839.831566.jpg

    Tap insert photo or video
    Mail app doesn't always send mail with attachment-imageuploadedbytapatalk1414455904.347408.jpg

    Tadaa
    Mail app doesn't always send mail with attachment-imageuploadedbytapatalk1414455926.998238.jpg


    Sent from my ancient but trustworthy iPhone 5.
    10-27-2014 07:25 PM
  5. mikedaub's Avatar
    Have you checked the address being sent from. Also, have you tried attaching the photo in the mail app, rather than from Photos?
    Sent from my ancient but trustworthy iPhone 5.
    I never thought of trying from one of the other 3 email addresses, so I tried last night. I got it to work with 1 of the others, but now, nothing. Very strange. When I attach them inline, they do send from any of the email addresses.

    This however, is the first time I have seen this. When going through the mailboxes in the app, I found an "outbox" app that only seems to appear when a message is sending, and when I went in there, BOOM!!! all of those emails I have been trying to send. Interestingly enough, when I add the photo inline, it never hits that outbox as it never pops up in the list while I watch for it.

    Mail app doesn't always send mail with attachment-image1.jpg

    When I click on any of those little red !, it just says there was an error. As soon as I exit the mailbox, if there is nothing currently being sent, I can't find it again.

    Somehow I manage to break something that works for everyone else. YAY me!!
    10-28-2014 08:46 AM
  6. Ledsteplin's Avatar
    I never thought of trying from one of the other 3 email addresses, so I tried last night. I got it to work with 1 of the others, but now, nothing. Very strange. When I attach them inline, they do send from any of the email addresses.

    This however, is the first time I have seen this. When going through the mailboxes in the app, I found an "outbox" app that only seems to appear when a message is sending, and when I went in there, BOOM!!! all of those emails I have been trying to send. Interestingly enough, when I add the photo inline, it never hits that outbox as it never pops up in the list while I watch for it.

    Click image for larger version. 

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    When I click on any of those little red !, it just says there was an error. As soon as I exit the mailbox, if there is nothing currently being sent, I can't find it again.

    Somehow I manage to break something that works for everyone else. YAY me!!
    I never see my sent email, unless I go to Sent. I used to, but got tired of seeing the same email twice on the inbox. I see "Outbox" some, but it vanishes and Sent is where I see my sent mail. Can you change the behavior in settings? Do you have "Always Bcc Myself" toggled on?


    Sent from my ancient but trustworthy iPhone 5.
    10-28-2014 12:06 PM
  7. mikedaub's Avatar
    I never see my sent email, unless I go to Sent. I used to, but got tired of seeing the same email twice on the inbox. I see "Outbox" some, but it vanishes and Sent is where I see my sent mail. Can you change the behavior in settings? Do you have "Always Bcc Myself" toggled on?


    Sent from my ancient but trustworthy iPhone 5.
    Hah..sorry. I was sending all those emails to myself just to test. Sorry about the confusion. I only see the sent messages in the sent box (unless I can catch them in the outbox).

    Maybe I just need to scrap the stock mail app and use the Gmail one, or something else. I just prefer how the notification for the Mail app shows up on the pebble..
    10-28-2014 12:46 PM
  8. Ledsteplin's Avatar
    Hah..sorry. I was sending all those emails to myself just to test. Sorry about the confusion. I only see the sent messages in the sent box (unless I can catch them in the outbox).

    Maybe I just need to scrap the stock mail app and use the Gmail one, or something else. I just prefer how the notification for the Mail app shows up on the pebble..
    Are you saying that even with "Always Bcc Myself" toggled on, you only see your sent email in "Sent"?


    Sent from my ancient but trustworthy iPhone 5.
    10-29-2014 08:55 AM
  9. mikedaub's Avatar
    Are you saying that even with "Always Bcc Myself" toggled on, you only see your sent email in "Sent"?


    Sent from my ancient but trustworthy iPhone 5.
    Not 100% sure. I have never clicked the "Bcc Myself" option.

    I guess this whole thing just baffles me since it works the proper way on my iPad, which I used the same steps and confirmed settings with the iPhone..

    Goofy technology.
    10-29-2014 09:02 AM

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