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Small Business Server Support Forum    
Subject: iPhone for business?
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David Smout User is Offline
United Kingdom
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6/26/2007

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11/26/2007 02:39 PM  
Hi, I have users here who are very interested in using an iPhone. We have a fairly standard SBS2003 Premium with RWW running.

The big selling point here is usability, all the 'smart' phones we have tried all fall down on the interface. We have some technophobes who need this kind of mobile access to email, contacts and calendar and I wanted to know how well it was working for others.

Add to that a good 'no limits' data policy from O2 and we don't have to worry about the scary data costs.

All opinons gratefully appreciated.

David.
Jack Hodson User is Offline
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11/26/2007 03:25 PM  
I would wait until they include 3G connectivity like most other mobiles. There is no data limit on the GPRS/EDGE network because no matter if you tried, its is too slow to reach it ;)

But the no limit on the 7.5K hotspots is good and will be perfect for email etc.
David Smout User is Offline
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11/26/2007 04:08 PM  
Hi, thanks for the reply.

I've read quite a lot across various 3G forums and also GPS ones too! Two things Apple appeared to have left out. One thing both groups appear to agree on though is that to keep the 8 hour talk time it's unlikely to appear any time soon on an iphone. It is just too power hungry, heat is also a problem for the GPS side of things.

The wifi seems to be the more likely way of updating data and we have wifi coverage over both our sites as we use Wifi mobile phones from Avaya. So on site is covered. The few users I have found using the 2.5g network say it's not blazing but it is pretty stable and useable. 3g seems to be quite flaky in comparison. I should say I'm in Scotland so 3g coverage is never going to be any good. Population density isn't really making commercial sense outside Glasgow and Edinburgh.

As I said every Windows and Symbian phone i've seen and used isn't a patch on this for simplicity of use. I'd rather have a slower data connection for my users than something they curse and swear at and come back to me time and time again as it has fallen over/refuses to sync/lost it's settings etc. We have a lot of Apple hardware here as well as PC's and I hardly ever have to glance at it by way of support. Most of it has been running 24/7 for the last 3 years without blinking. That speaks volumes to me.

Bottom line is I'm the only support person for quite a large 'small' business and we do a lot of other things which are out of the mainstream, like new media art, which i also support. So if it integrates reasonably well using IMAP over SSL and you can do everything any other phone can without it freezing and needing users to consult manuals every two minutes I'll be very happy indeed. :D

Jack Hodson User is Offline
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11/26/2007 04:20 PM  
If it works as well as my MacBook I woudl be happy too, easy computing! I am sure Eriq will be able to reveal how well the IMPA over SSL works - had a go setting up my Sony Ericsson w850i on this the other day, but no joy :(
David Smout User is Offline
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11/26/2007 06:07 PM  
You know i'd be happy if it even syncs with the users PC with out falling over. Every bloomin one of the different devices/phones we've had at some point needs hours of fiddling to do that simple task. There are some that still refuse and I run out of time and patience.
Eriq Neale User is Offline
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12/04/2007 06:36 PM  
Sorry to be late into the thread, but I"m just now getting caught up from my travel.

Remember that Apple considers the iPhone to be a consumer device, not a business device. So any business functionality that you're able to get out of it is a complete side-effect. That being said, IMAP over SSL to an SBS box from the iPhone works well, and what I've seen of syncing calendar/contact information through iTunes seems to be OK as well. A lot of that will depend on how the PCs are set up, etc., but it shoudl work.

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
David Smout User is Offline
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12/05/2007 11:48 AM  
Hi Eriq,

Thanks for the reply, excellent walkthrough and i've used the links from SBS Diva too as we've gone down the GoDaddy route for a certificate. Not quite finished it yet as complications with the Registrant details. we've recently changed our company name and our domains are managed by another company so not a speedy business.

I can confirm that my CEO's iPhone happily syncs using iTunes, the initial set up took ages using a Dell Latitude D600. It would be interesting to try it on a much newer machine. But once done it all works.

I'm crossing my fingers saying this but I like it so much more than any windows mobile device I've used. Had my doubts about using Itunes but it's good. Should have the imap stuff tested later on today and will update this thread then.

If this is Apple's idea of a consumer device then Blackberry et al should be very worried if they do start looking at business applications as it does business rather well. (at the moment ;-)  )

David Smout User is Offline
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12/07/2007 11:25 AM  
this came through from IT Pro newsletter today, it's certainly made an impact on the business market whether intentional or not.

http://www.itpro.co.uk/news/144321/sap-goes-web-20-with-iphonefriendly-software.html
David Smout User is Offline
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12/12/2007 04:19 PM  
Hi Eriq,

Finally installed the certificate on the server and it is working with all our remote websites. But, I haven't been able to try the iphone yet. I can't get it off the CEO! She must like it too much, can't blame her.

Anyhow, I tried using Mail on a mac mini I had sitting about on the public wifi network we have in the building. It's a separate connection from the business network. i can browse to the RWW site fine and check my email etc using Safari so the connection is ok and the certificate works.

When I try setting up IMAP account in Mail it fails. I used the walk through from Tim Barrett for the iPhone settings.

I opened the correct ports on my Firebox (143 and 993) and used it to monitor when Imap got a hit. Interestingly only the port 993 showed traffic, not 143.

Another confusion is the bit in Tims walk through which mentions port 587! I have read it is the alternative port to 25 and I also noticed it is the outgoing server port default in Mac's Mail program.

Is this the root of the problem? If I open 587 on my Firebox will ISA still prevent the connection?

Hope you can help.
David Smout User is Offline
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12/12/2007 06:19 PM  
Hi, I just set up 587 on my Firebox and sent a message from Mail. Bingo! it showed traffic through that port. So that is traffic on 993 and 587 but nothing on 143.

Still none the wiser after that.

David.
Eriq Neale User is Offline
Texas, USA
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Microsoft MVP
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12/18/2007 02:20 PM  
David -

there will not be any traffic on port 143 if you have IMAP SSL enabled on the iPhone. This is exactly what you want, by the way, and should stop forwarding port 143. Since you're getting traffic on port 993, that means the iPhone is making connections using IMAP SSL, and if it can conect on port 993, it will not attempt to use port 143.

587 is the SSL port for SMTP, so again, if that's working after opening the port, you're in good shape.

Basically, you're working exactly as expected now. All is good!

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
David Smout User is Offline
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12/24/2007 12:49 PM  
Cheers Eriq, all makes sense. I haven't been able to play with the CEO's iPhone since the last post.

I have tested with a mac using mail and still no joy using IMAP over SSL. Bit stuck now.

The good news is the CEO loves the iPhone so much we now have 3 extra ones and one of them is mine. Big BUT. In the UK, O2 the operator has a problem activating iPhones for business accounts. mine is sitting here dead after 3 days. We used one of the other business credit cards we have to buy the three and it won't let us past the £100 deposit screen. It is making my blood boil a little.

I'm annoyed at the line they punt out that it isn't a business tool, despite the head of Google and rather a lot of other business folk waving them around, add to that Avaya have announced they are porting their one-x mobile to the iPhone in early 2008. We have an Avaya system using Wifi phones and IP desk phones so it makes it a very nice proposition for us.

I digress, need to work out why the IMAP request is getting through the Firebox but failing at the 2003SBS box.

happy holidays.

David.
David Smout User is Offline
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12/24/2007 03:44 PM  
wee update, iPhones all finally authenticated on O2 network but no joy on the imap connection. vexing in the extreme. I've tried it on two wifi networks and no joy.

David.
Eriq Neale User is Offline
Texas, USA
Member since
5/3/2005

Microsoft MVP
Posts: 2105

12/25/2007 03:33 PM  
David -

Have you got the GoDaddy certs installed on the SBS box yet? Until you do, the iPhone will NOT be able to make a secure IMAP connection on port 993. There is no mechanism to install a cert on the iPhone like there are on other devices, so if the SSL cert is not from a vendor that the iPhone recognizes, it will refuse to connect.

Easiest way to check for basic connectivity is to try to connect to OWA from the iPhone (i.e., https://server.domain.com/exchange) and see if the iPhone chokes on the cert. If it does, it won't do IMAP/SSL. If it doesn't, there's something else going on.

If you like, you can PM me the URL of the server in question and I can do some basic checking on this end for IMAP/SSL connectivity.

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
David Smout User is Offline
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12/28/2007 02:04 PM  
hi. No problem with cert now. Using iPhone to post this having followed the link from the notification email in my OWA inbox. Thanks for the kind offer of help Eriq. Just to be sure i will run over things again before I call for the cavalry.
David Smout User is Offline
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12/31/2007 12:05 PM  
Hi Eriq,
Finally made it into the office tinker with the Firewall, didn't want to do that remotely in case of disaster, i live on the other side of the country so didn't fancy a festive dash over here.

Discovered that the Firewall was blocking the ports, well, the setting on the port wasn't set to Client. re-did the policy on 993 and hey presto it worked. Now though it appears to want to do the SMTP stuff over 25 and not 587. i've tried using the colon at the end of the FQDN and port number 587 in the settings on that mail account but still no joy.

The SMTP Port 25 on our Firewalll is locked down quite tightly, it only listens for our ISP mail servers and it is nat'ed to our Exchange server, outgoing is from our server back to the ISP mail servers. Could this be the problem?

I've added an Alt-SMTP fro SSL on port 587 and set it to a client port. That is more open, it listens for any traffic and nats to the server, outgoing is from any to external.

Any thoughts?
Eriq Neale User is Offline
Texas, USA
Member since
5/3/2005

Microsoft MVP
Posts: 2105

12/31/2007 01:52 PM  
David -

Thought that the firewall might be part of the problem. On the iPhone, you need to make sure that the SSL settings for both IMAP and SSL are set to ON to get the iPhone to try and connect using port 587, but you can also use the ":587" settings to try and force the issue as well. But the way you have the firewall set for 587 should work, provided 587 is listening correctly on the sever.

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
David Smout User is Offline
United Kingdom
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12/31/2007 02:10 PM  
aha, I have spoken to our ISP who support the firewall and we ran some tests. It looks like although the iPhone tries on 587 it will try on 25 if that fails. We added the ip address of the phone to the SMTP port settings and data flowed, but the headers were stripped out by the SMTP proxy policy.

It does look like it is now my SBS server, or ISA to be specific which is now the blockage. I didn't realise I would need another rule there for 587. I'll add one and see what happens. There are two SMTP rules there already, one for access and one for outbound. Excuse my lack of knowledge on this, when the device sends an email, is it talking to the server through the 587 port but it is Exchange who sends the email through the normal port 25? If so a simple access rule should be ok to get things moving.

Thanks for your time on this.

David.
David Smout User is Offline
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12/31/2007 02:16 PM  
Hmmm, tried the same method as the IMAPS server, but using SMTPS. This is on port 465 though.
Eriq Neale User is Offline
Texas, USA
Member since
5/3/2005

Microsoft MVP
Posts: 2105

12/31/2007 02:16 PM  
Oh, yeah, you will. Sorry, I completely forgot ISA was on the box. yes, ISA will have to have a rule to allow port 587 through. Did I not include that in the instructions? I thought I had. I'll take a look and update if necessary.

Yes, Exchange will receive the e-mail from the iPhone on port 587 and accept it into the system. But if it's a message that needs to get sent back out to someone else, Exchange will send it out on port 25 as it does with all other mail.

You also don't want to try to permanently add the IP of the iPhone to the firewall rules, as I seriously doubt that that iPhone has a static IP assigned to it. It was good to do that as a test to see where things were breaking, but if you haven't already, you should go ahead and remove that IP from the firewall. once you get the ISA rule for 587, you should be in good shape.

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
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