Become a MacRumors Supporter for $50/year with no ads, ability to filter front page stories, and private forums.

bartonjd

macrumors member
Original poster
Oct 18, 2012
73
0
Logan, Utah
I have been sniffing my iPhone traffic of late and yesterday made an uncomfortable discovery, my gmail password is being sent to google in plain text! I have been through every setting I can find and as near as I can tell, SSL is turned on everywhere, is this a weakness with IOS or is there something I am missing? Thanks in advance!
 
Don't use on unsecure networks.

Cellular, home wifi, or VPN to home.
 
Don't use on unsecure networks.

Cellular, home wifi, or VPN to home.

This. From past sniffing, it's a GMAIL thing. I was able to see the password, plain text being sent from a Mac on a home WPA2 secure network.
 
This. From past sniffing, it's a GMAIL thing. I was able to see the password, plain text being sent from a Mac on a home WPA2 secure network.
So Gmail doesn't use SSL for sending the password despite it's being set in the settings app?

Is this with the web interface or native iOS Mail app?

This was with the built in mail app not the web interface.

So is it fair to say I should use a different mail app, or am I going to experience this no matter what?
 
I'd like to try and reproduce this. Did you sniff via a shared network connection or is there a better way now (it's been a while since I've done this). Also, what iOS version are you on and did you set up the account as a Google account or Exchange ActiveSync or something else? Also, could it be an app (other than the mail app). A quick test would be to disable or remove the Gmail e-mail account.

Sorry for all the questions but not much point in trying if my setup is too dissimilar.
 
So Gmail doesn't use SSL for sending the password despite it's being set in the settings app?



This was with the built in mail app not the web interface.

So is it fair to say I should use a different mail app, or am I going to experience this no matter what?

Not sure. All I know is this is the third instance I have heard of this, one of them was my own password being seen during a wifi sniffing experiment of my own, with a friend, using a secure network. The password was found and seen in the logs in plain text.
 
I'd like to try and reproduce this. Did you sniff via a shared network connection or is there a better way now (it's been a while since I've done this). Also, what iOS version are you on and did you set up the account as a Google account or Exchange ActiveSync or something else? Also, could it be an app (other than the mail app). A quick test would be to disable or remove the Gmail e-mail account.

Sorry for all the questions but not much point in trying if my setup is too dissimilar.

I am definitely using the native Mail app, I am on iOS 7.1 beta 3, so its possible the beta is the issue. I set this up as traditional Google account, I wasn't aware you could still set a gmail account up using the exchange option. I am using Cain & Abel for the traffic analysis.

Not sure. All I know is this is the third instance I have heard of this, one of them was my own password being seen during a wifi sniffing experiment of my own, with a friend, using a secure network. The password was found and seen in the logs in plain text.

I am interested to hear more, what incidents have you heard of?
 
Last edited:
In this day and age do not expect any internet privacy.


This isn't so much about privacy as not wanting my password blatantly stolen... At least not as easily as Apple is making it. I'd appreciate any recommendations on how I can check Gmail securely without using safari to do it.
 
This isn't so much about privacy as not wanting my password blatantly stolen... At least not as easily as Apple is making it. I'd appreciate any recommendations on how I can check Gmail securely without using safari to do it.

Have you tried the Gmail app?
 
Can you please clarify what you are saying? Is the password being sent in plaintext via SSL or is it being sent without encryption at all?

Both of these are problems but the latter is far more serious. How are you sniffing the traffic?
 
Have you tried the Gmail app?

I have not... I didnt like the gmail app when I used it but perhaps I need to reconsider.

Can you please clarify what you are saying? Is the password being sent in plaintext via SSL or is it being sent without encryption at all?

Both of these are problems but the latter is far more serious. How are you sniffing the traffic?

It is definitely plaintext, but isn't this a concern SSL or not, my sniffer program shouldn't be able to see the password should it? I am using the sniffer tab in Cain and Abel and choosing my router and then redirecting my iPhones IP to C&A.
 
I have not... I didnt like the gmail app when I used it but perhaps I need to reconsider.



It is definitely plaintext, but isn't this a concern SSL or not, my sniffer program shouldn't be able to see the password should it? I am using the sniffer tab in Cain and Abel and choosing my router and then redirecting my iPhones IP to C&A.

I was just wondering about the Gmail app. If the Gmail app is written as a native app, then it might suffer from the same problem as the iOS mail app since they would utilize the same API.

By the way, do you know how to determine if an app is native or web interface?
 
It is definitely plaintext, but isn't this a concern SSL or not, my sniffer program shouldn't be able to see the password should it? I am using the sniffer tab in Cain and Abel and choosing my router and then redirecting my iPhones IP to C&A.
If Cain and Abel is proxying SSL, then yes, it'll see everything.

When you say you're redirecting your iPhones ip to C&A, are you talking about arp poisoning?
 
Last edited:
This raises lots of questions.

How exactly is the data stream being sniffed? What is the procedure used for this observation?

Is anything else in the message observable, besides the password?

Is two-factor authentication turned on in the user's Gmail account?

Is the password usable? ...In other words, does it allow a third party on a different machine to access the Gmail account in someway? (This would be the acid test for two-factor authentication.)
 
What version of iOS are you running?

I'm on iOS 7.0.4 and the default Mail app says it's using token authentication.

I haven't check the traffic sent though.
 
Any records of this happening in the past? I'd think it's a front page news if true.
So the OP's using a tool called Cain and Abel, which has this ability (emphasis mine):

The latest version is faster and contains a lot of new features like APR (Arp Poison Routing) which enables sniffing on switched LANs and Man-in-the-Middle attacks. The sniffer in this version can also analyze encrypted protocols such as SSH-1 and HTTPS, and contains filters to capture credentials from a wide range of authentication mechanisms.
 
Thanks. The OP made it sound like they weren't encrypted in the first place. Paranoid much?

I don't know that being concerned about broadcasting your password in plaintext is being paranoid. Perhaps I'm not as well informed in the areas of sniffing and traffic analysis, but I think it is a worthwhile concern and not overly paranoid.


Thanks. The OP made it sound like they weren't encrypted in the first place. Paranoid much?

If Cain and Abel is proxying SSL, then yes, it'll see everything.

When you say you're redirecting your iPhones ip to C&A, are you talking about arp poisoning?

Yes it is ARP poisoning. So if C&A is providing the cert, it is ok that the password shows up as plaintext?

I haven;t experienced this with Evomail, which I have been trying out this week.
 
Yes it is ARP poisoning. So if C&A is providing the cert, it is ok that the password shows up as plaintext?
Yes.

The cert that C&A provides is bogus (not signed by a trusted certificate authority, hostname mismatch, etc) and your iPhone should have warned you of this dangerous situation.

photo-3.png


Only if you clicked the Continue button should the iPhone have used the bogus C&A cert, which is required for C&A to decrypt your SSL-encrypted data.

IIRC, when we were playing around with C&A, every major website we tried logging into (using https://) "only" used SSL to encrypt the username/password/data. Meaning that if someone fell for a C&A MITM attack, everything would show as plain text.
 
Yes.

The cert that C&A provides is bogus (not signed by a trusted certificate authority, hostname mismatch, etc) and your iPhone should have warned you of this dangerous situation.

photo-3.png


Only if you clicked the Continue button should the iPhone have used the bogus C&A cert, which is required for C&A to decrypt your SSL-encrypted data.

IIRC, when we were playing around with C&A, every major website we tried logging into (using https://) "only" used SSL to encrypt the username/password/data. Meaning that if someone fell for a C&A MITM attack, everything would show as plain text.

I see now.
That makes sense then how and why.
 
Thanks for the responses, this brings me some peace of mind, and a bit of a laugh too... I remember accepting the cert now that you post the screenshot.... Whoops
 
Thanks for the responses, this brings me some peace of mind, and a bit of a laugh too... I remember accepting the cert now that you post the screenshot.... Whoops

Very big relief. Thanks, everybody, for getting to the bottom of that. Thanks to the OP for raising the issue, too. I'm sure a lot of visitors to this thread learned something.

It's also a nice reminder to pay attention to those certificate pop-up. They're a valuable indicator that something is amiss that may indicate your security is compromised.
 
Register on MacRumors! This sidebar will go away, and you'll see fewer ads.