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Writer's pictureairwatchhk

Using Fiddler Proxy for Mobile Email Troubleshooting

Updated: Jul 12

I have shown you how to set up Fiddler Poxy in my preivous post: https://airwatchhk.wixsite.com/euc852/post/proxy-intercepting-using-fiddler-on-ios


In this post, I am going to show you how to use Fiddler to do Boxer and native email troubleshooting.


MEM are evolving and is becoming not pure ActiveSync based.


For example, Office 365 are now Modern Authentication based.


There are also many other moving parts in mobile email synchronization. For instance, Email Notification Service (ENS) and Azure Information Protection Labeling (AIP). They are both on Exchange Web Service based (EWS).


In addition to proxy interception, you can also look at email client log if you are on Boxer. This is probably one of the good reasons to use Boxer over other email client as it provides a convenient way to do trouble shooting.


A more advanced way to trouble shoot mobile email issues is to look at the traffic going back and forth between the email client and the email backend.


As mobile email traffic are all web based protocol, we can use porxy interception to have a close look and this helps a lot when it comes to troubleshooting.



This is vidoe on snooping iOS Boxer traffic :



This is vidoe on snooping iOS native email traffic :



The same trick applies to Android as well.


In case you encounter server identity warning and certificate not trusted warning like , please follow this to get a new fiddler root certificate generated. https://www.telerik.com/blogs/the-certenroll-certificate-generator


Get the new root certificate downloaded again to your iPhone and problem should be gone after iPhone receive a new root certificate.



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