S/MIME on iPhone 4S: certificates, keys in Mail fail to offer Install option

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S/MIME on iPhone 4S: certificates, keys in Mail fail to offer Install option

iPhone 4S, iOS 9.3.6 (13G37)

tl;dr: upon sending myself a certificate and/or private key from my Mac to Mail and opening the incoming email, then tapping the attachment, there is No Offer by iOS to install anything, when every online article i see says that’s what’s supposed to happen and glosses over this step. WTF?

Full Story:

I’ve been using self-signed S/MIME certificates on Apple Mail for Mac since the late 2000s. In fact, i wrote an article on this subject. Until now, i’ve never included information on iOS and (related small device OSes), due to time constraints, disinterest, and not owning any such devices. I’m trying to get this working, both for personal usage and to update my article. I’ve been given a hand-me-down iPhone 4S, which is all clean install set up. Mail works fine, unencrypted.

Several articles online appearing to cover iOS 7 through at least iOS 10 if not later indicate that a person emails a .p12 file with their (established working) certificate and private key from the Mac to the iPhone, then opens that incoming email on the iPhone. A single tap of the .p12 attachment is supposed to bring up an offer to install a certificate or profile (wording differs). Screenshots of what they’re showing are available in the linked articles, and i don’t think i’m allowed to repost those here. I recommend the first link and scroll down to Tip #2.

Here’s what i get instead, starting with the initial screen before i tap anything:

So per the instructions on every site i’ve found, i single tap Certificates.p12. The articles tell me i should see an installation option. Instead i see:

The top More option is unhelpful:

Similarly for the bottom More:

The above was for a combined certificate and private key in the .p12 file. Here is how it initially looked when i made separate .cer and .p12 files, for the certificate and private key respectively:

Tapping on either of these items produced the exact same unhelpful result as in the first example of the combined file.

Why is iOS 9.3.6 on my iPhone 4S failing to offer any option to install?

iPhone 4s, iOS 9

Posted on Aug 8, 2020 4:34 PM

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Answer 1

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Sonic Purity Author

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22 points

Aug 14, 2020 1:33 PM in response to Sonic Purity

Replying to myself: eventually figured it out. While it saddens me that no one here was able to help, appreciation to anyone who at least read this question.

Answer: there was a profile installed for the email account in question, which was blocking all sorts of functionality.

The profile was provided by my email service provider (ESP) to make setup easier. I thought i needed to keep it, being unfamiliar with the concept of profiles on iOS. I learned from a more careful reading of the first page of one of the articles linked above of the importance of deleting profiles which may conflict.

Rereading instructions from my ESP, i learned that there was an option for manual email account setup. So, i made a backup of my iPhone, deleted the profile (which deleted the email account from Mail on the iPhone), then manually set up the account per my ESP’s instructions. After doing that, i was successfully able to import a certificate via email and install it as described in the linked articles.

Issue resolved.

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S/MIME on iPhone 4S: certificates, keys in Mail fail to offer Install option

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