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Chewie

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My preliminary iPhone experience written by a guy who hasn't seen one yet.

Hypothetical situation regarding a company that like a lot of companies doesn't allow SMTP access through their corporate firewall.

Let's just say in this situation the IT team is looking at how to allow employees access to SMTP from outside the corporate firewall, but the IT guy's boss is on vacation and the server in question is 7 hours away, and it's a Monday, so said IT guy doesn't want to break the server and possibly lock himself out of remote access, and hose everyone's email for a day or more. Like I said though this is all a hypothetical situation. :D

So in the meantime you want to set up email on your iPhone and you can receive email fine, but since your corporate firewall blocks SMTP you can't send emails using your work's mail server.

What does the typical user need to do then to send email?

The best thing I've found so far is to use a Gmail account. If you don't have a Gmail account, go to http://mail.google.com/mail/signup and register. It's free and you don't have receive an invite anymore to get a Gmail account. Even if you have a Gmail account I would recommend signing up for another one because we are going to set it up to appear as if it's your work email account.

Why Gmail.
Gmail is free.
Cause I don't know what the SMTP settings for Yahoo, or Hotmail are, or if they even allow you to access them with their free services.
Gmail has been confirmed to work while connected to AT&T's mobile EDGE network and while connected to WI-FI networks.
Google isn't evil (Not yet at least)
AT&T's SMTP server only works while connected to the EDGE network. Lame.

The following could very well work with AOL accounts and their SMTP server. Sort of tried but, it didn't work the first time we tried and I didn't want to tech it over the phone. I had plenty of google results telling me gmail works and no positive confirmations AOL works.

Kind of works with .Mac but .Mac sends the email as your .Mac address with your work's address as the reply address. Not nearly as transparent to your recipients and may confuse them.

Here is the beauty of the Gmail SMTP server. It doesn't care if it's an iPhone or the Mac OSX email program, Thunderbird, Outlook, Opera, etc. The same settings that allow the iPhone to send using Gmail's SMTP server will work with any email program whether it be a laptop, desktop or mobile phone email program.

First things first

Log into Gmail in a browser from a computer.
In the upper right corner click on Settings
Click on the Accounts tab
Click on Add another email address

A pop up will open. Type in your full name and [email protected]
Click Next Step >>
Click Send Verification

Check your work email and click on the verification link in the email you just got from Gmail.

That should give you a message saying it worked. Go back to your Gmail account and click on Settings

Click on the Accounts tab again.

Now you should see your Gmail address and work email address
Click on "make default" next to your work account

From this moment on any mail you send from the Gmail account will appear to come from your work address.

That's the first step.

At this point I'm assuming your iPhone has been synced with the computer and the email settings have been transferred over to the phone. I'm also assuming email can be received with those settings. At this point we need to change the SMTP (Outgoing) server so it uses Gmail instead of your work mail outgoing mail server.

From the Home menu, tap Settings.
Select your work account
Scroll to the bottom of the page and tap Advanced.

All we need to mess with is the Outgoing settings. Leave incoming alone if it works.
Outgoing server should be smtp.gmail.com
Make sure Outgoing is set to use SSL
Outgoing Authentication needs to be set to Password.
Enter in your Gmail address ([email protected]) as the user name and Gmail password for the password in the Outgoing settings.

Another option is to initially setup your computer's email program with Gmail's SMTP settings and then resync the iPhone. It should work just as well, but I haven't tested this out.

These settings should work but since I haven't seen the settings myself and relied on people typing in things as I tell them to I can't guarantee it. So far though two users down and one to go so I'm fairly confident this all works.

Also one user setup his Gmail account to forward all incoming email to his work account just in case somehow someone replied to his Gmail account instead of his work account. It shouldn't be a problem, but it could conceivably happen.

I think I also read there is a way to sync the Gmail Sent mail folder with your work Sent mail folder but that will have to wait till I actually have an iPhone in my hands to play with.
 

Psychicpet

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Joined
Aug 16, 2003
Messages
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Location
Sylvan Lake, Alberta, Canada
"SMTP IT IP.... waaahhh, I can't take any more"
fg_paulie_02.jpg



:p
 

phatduckk

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Joined
Jul 25, 2004
Messages
8,145
Location
San Mateo, California, United States
here's what id do. this list is in order of my thinking of the solutions off the top of my head..

OPTION 1:

ya - i would have done the same thing as you except i have my own domain and server so id use that smtp instead of gmail. same difference tho.

OPTION 2:

can you specifcy a port on the iPhone when configuring an SMTP server? you could technically put your smtp on a high port and assume that will keep attacks away. its not good to assume but for the most part a random high port (3366 etc) with authentication would be pretty safe.

OPTION 3 (probably the best one)

You could configure STMP to work with only certain mac addresses. actually - it would be easier to do that on a firewall. So have the firewall use a whitelist of mac addresses (ex: BP's iPhone's Mac Address) to determine whether it should accept or reject the request.

option 3 seems the cleanest to me. wacha think chewie?
 

Chewie

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Jan 24, 2005
Messages
324
Location
San Luis Obispo, CA
Yeah, kind of just thinking at loud and passing on what I've learned so far for the greater good of the iPhone community. In fact I just checked the eb webmaster email account and someone googled and found the post and asked me a question.

I like the idea of the extra layer of security the MAC Address brings though. Is that gonna work via the EDGE network though? I'm kind of still in the dark when it comes to these new fangled cell phones. I can make calls and text on mine. I even have a camera on my phone now so I can take crappy under lit and out of focus pictures of my friends when they are drunk. :)

Anyways at this point I lack hands on experience about how the iPhone networking works. Specifically even if we do add some security features, loosen up the firewall, will our SMTP settings work both on the EDGE network and on WI-FI hotspots. I know I can setup up a WI-FI hotspot here in the SLO office and make that work no problem, but is it gonna work for our Warped tour stage manager when he's on the road in B.F.E. using a Mac D's hotspot or he's completely on EDGE. I assume it would work on both EDGE and WI-FI networks, but why does AT&T's own SMTP server only work on EDGE? My gut tells me that's just piss poor planning on AT&T's part, but it's a lingering question in my head.

Maybe I should go bug the crap out of the Abercrombie & Fitch wearing metros that work in the Apple store today. Did I say that out loud? Maybe I'll make the iPhone display reboot so I can ask them really loud questions about why that display is booting Windows XP. Uh-oh I already made myself hungry. Tri-Tip tacos exactly one block away at Firestone's. mmmmmmmmm. Oh man if they had breakfast tri-tip tacos. I guess it's time to hit A2 on the vending machine. Definitely time for some caffeine.
 

phatduckk

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Jul 25, 2004
Messages
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Location
San Mateo, California, United States
Yeah, kind of just thinking at loud and passing on what I've learned so far for the greater good of the iPhone community. In fact I just checked the eb webmaster email account and someone googled and found the post and asked me a question.

I like the idea of the extra layer of security the MAC Address brings though. Is that gonna work via the EDGE network though? I'm kind of still in the dark when it comes to these new fangled cell phones. I can make calls and text on mine. I even have a camera on my phone now so I can take crappy under lit and out of focus pictures of my friends when they are drunk. :)

Anyways at this point I lack hands on experience about how the iPhone networking works. Specifically even if we do add some security features, loosen up the firewall, will our SMTP settings work both on the EDGE network and on WI-FI hotspots. I know I can setup up a WI-FI hotspot here in the SLO office and make that work no problem, but is it gonna work for our Warped tour stage manager when he's on the road in B.F.E. using a Mac D's hotspot or he's completely on EDGE. I assume it would work on both EDGE and WI-FI networks, but why does AT&T's own SMTP server only work on EDGE? My gut tells me that's just piss poor planning on AT&T's part, but it's a lingering question in my head.

Maybe I should go bug the crap out of the Abercrombie & Fitch wearing metros that work in the Apple store today. Did I say that out loud? Maybe I'll make the iPhone display reboot so I can ask them really loud questions about why that display is booting Windows XP. Uh-oh I already made myself hungry. Tri-Tip tacos exactly one block away at Firestone's. mmmmmmmmm. Oh man if they had breakfast tri-tip tacos. I guess it's time to hit A2 on the vending machine. Definitely time for some caffeine.

i dont see why not. the easiest way to test how the firewall and the edge network play together would be to set up some worthless install of apache on port 8080 or something else unused.

then make sure the apache install works from your computer... so go to http://<whatever>:8080. If the computer works then try accessing http://<whatever>:8080 thru safari on the iPhone (make sure its got wifi off)

OK assuming that worked - place a firewall rule that blocks access to 8080 for everything.

now http://<whatever>:8080 should NOT work form the iPhone or any othe computer ever.

Now change the firewall rule to allow access to 8080 to the iPhone's MAC address. again, try accessing http://<whatever>:8080 thru safari on the iPhone (with wifi off - so its over edge)

if that works. you're almost home - just go back to the firewall and change port 8080 to port 25. then SMTP should work just fine.

After that ditch the apache install.

It would actually be easiest to give your workstation a public IP and do the apache setup stuff there. that way you wont have to bother with uninstalling it

i think this will work. shouldnt be too hard depending on what firewall youre using and how easy its admin interface is.

Hell - you could honestly do this on a crappy LinkSys in 10 minutes.
 

phatduckk

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does this bs mean that my iphone can act like my blackberry?

moreso than currently. assuming what i mentioned to chewie works (which i think it should) then assuming you can use IMAP on the iPhone, then i dont see why not. with IMAP emails you send off your iPhone will end up in the sent box on the server too.

right it pretty much sounds liek chewie is concerned about security which is obviously a good thing.

I dont have an iPhone and dunno all the settings etc - but i think this would work like a blackberry if my assumptions are correct.

NOW i did read that when sending email from an iPhone you cant pick which account to compose a new message from. I dunno if this is true - but that sucks. however if you only use it for MM mail its a non issue. if youre gonna use it for more (personal mail too) then we'd have to look into it
 

phatduckk

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Messages
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Location
San Mateo, California, United States
ok after reading some stuff for like 10 minutes im gonna say this should work pretty well.

push email wont work for you tho. What's that mean? your phone will NOT be instantly notified by your email servers that you have new mail. You're gonna have to set your iPhone to check your emails every 15 minutes. So, this is different than the bberry - but unless you need your emails instantly it shouldnt be a big deal considering the phone is gonna check your email every 15 minutes anyways. so in essence you're gonna have a 15 minute email delay. there is NO good way around this. tho i know of a lame solution

anywho... i say "yes it should work"
 

phatduckk

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San Mateo, California, United States
ok more info...

you should setup each email account to use IMAP.

FYI smtp means "outgoing mail serevr"

AOL's IMAP address is: imap.aol.com
AOL SMTP server is: smtp.aol.com
AOL SMTP port is: 587

the .mac setup should be straightfoward im assuming since its an Apple product.

and the MM stuff is Chewie's deal... he's still working on the SMTP thing.
 

phatduckk

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San Mateo, California, United States
ok and i just did one more experiment which may or may not be an acceptabel solutions. You can use my SMTP server! I can sent you up a login and password.

So you can sent up all your email accounts on the iPhone to have IMAP for the incoming mail but just use my server to send your email. I dont mind. This way Chewie doesnt have to do stuff and if you use IMAP your messages will still end up in your real accounts "sent" folder.

No info will stay on my server - you'll just use it to send mail. i will NOT have any idea what youre sending.

if you guys just wanna use my server to send mail lemme know and ill setup a username and password. it'll take me 1 minute.
 
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