Go Anywhere OpenPGP Studio is a free, cross platform PGP encryption software for Windows, Mac, Linux. Having Symantecs proven technology at its core, the Encryption Desktop utility relies on user-generated PGP keys to protect important information that is transferred from and to email clients, as. And some mobile apps can handle PGP-encrypted. But most of us don’t live in a walled garden, and one of the company’s founders, Phil Zimmermann, is responsible nearly 25 years ago for turning public-key cryptography into. High Sierra: Mail tells LIES and disseminates Fake News!PGP on the Mac. Verify the authenticity of security notifications Encrypt messages to send to Apple via product-securityapple.com When not at a Mac or laptop and using mobile devices (iOS) we use an app called Secumail, which utilizes the same Open PGP keys created by GPG Suite to encrypt/decrypt mail, iMessages, clipboard.Note: To save on website hosting costs, screenshot images from other macOS/OS X versions (from other articles in this series) are used in this article when the only differences between the OS versions are cosmetic and minor, or involve commands or options not relevant to the current discussion.The High Sierra experience mostly looks and works like OS X 10.10 Yosemite and 10.11 El Capitan, and macOS 10.12 Sierra, with some minor user interface changes, such as squishing down the button bar inline with the window “stoplight” dots on incoming emails in separate windows, as was already the case in Mail 10 for Sierra for outgoing message forms. Hopefully this article will help you whack through them and get some good use out of Mail in High Sierra (or you could just stay with/revert to/move to Sierra). So much for the alternate year’s macOS release being a bugfix year! As well, other bugs remain.
Pgp Mail Sierra Mac Or LaptopIf you followed the instructions on this series of articles in the past (through end of August 2017) recommending omitting the KUE and have been living in a pre-Sierra Mac universe, you’re hosed: you need to make new self-signed certificates with a proper KUE.The following instructions have been formulated running macOS 10.13.6, its Mail 11.5, Safari 11.1.2, Keychain Access 10.0 (55237.50.3), Certificate Assistant 5.0 (55174.50.1), and all current updates to these items as of 4 September 2018. If you’ve used this set of articles after August 2017 to make your self-signed certificate, you’re good. If your existing certificates have the KUE, you’re good to go—and if you’ve been successfully using secure S/MIME email in Mac Mail in macOS 10.12 Sierra or newer, this is already true for you. Apple security documents reference vulnerabilities by CVE-ID when possible.As with macOS versions since 10.12 Sierra, Mail 11 and the security infrastructure in macOS 10.13 High Sierra require the Key Usage Extension (KUE) to exist and be properly filled out for there to be any hope of S/MIME to work in Mail. You can encrypt communications with Apple using the Apple Product Security PGP Key. For more information about security, see the Apple Product Security page. ![]() The biggest problem remains that Certificate Assistant never asks for/confirms the email address, without which the certificate is useless for email! In many (but not all) cases, Certificate Assistant fails to insert any email address whatsoever into a default certificate, rendering it useless for email. Starting with Keychain Access 10.0 and Certificate Assistant 5.0 (55174.50.1) included with macOS 10.13 High Sierra, Apple has made significant improvements, fixing a longstanding bug with broken-by-default Key Usage Extensions. Given that S/MIME (Email) is most definitely the Certificate Type we want, one might think that it would be OK to merely verify the name and click Continue. You’ll be presented with the Create Your Certificate window:Self Signed Root is exactly the type of certificate we wish to create. Certificate Assistant version 5.0 will run. From its eponymous menu, select Certificate Assistant and Create a Certificate…: The Create button changes to Continue. For all these reasons, be sure to check Let me override defaults. Most people will find renewing their certificate each year—and getting all their correspondents to renew it as well!—a huge hassle not worth undertaking. Creating a broken certificate then throwing on other layers in the keychain and/or Mail infrastructures to correct the issues does nothing to make the broken certificate valid on other systems—forget the other layers and have Certificate Assistant make proper certificates!Even if Apple hadn’t made the absent email address error which renders a default certificate useless for secure email, the default lifetime for the certificate is set for one year. Note that even though OS X versions 10.6 through 10.13 contain one or more added layers of complexity to work around these mistakes, these added layers are not backward-compatible with older OS X versions, nor in my testing with High Sierra and its Mail itself! It is also extremely unlikely to be compatible with non-Apple systems. Even with the significant progress of other major bugs being fixed, as of this writing, Apple has not fixed this intermittent (mostly failing) lack-of-email-address problem, all the way through the most recent version tested, OS 10.15 Catalina. The tradeoff with a longer time is that there is a much longer time span over which the valid certificate may be compromised by some malefactor getting ahold of your security credential set (certificate + public & private keys) and pretending to be you. I strongly recommend choosing a longer Validity Period, to minimize the hassle of re-creating a new certificate, distributing it to all your secure correspondents, and getting them to do the work to get the new one trusted on their system(s). If you think you may wind up having multiple certificates for the same user name and/or email address on one system, it is probably a good idea to ensure that the serial numbers differ (though i did not find any issues in brief testing where they were the same). The first of the series of detail windows— Certificate Information—asks you to fill in basic information:I have not found that the Serial Number matters, in my testing. Because of the necessity of overriding the defaults, you’ll now be presented with a series of detailed settings windows. ![]() The defaults of 2048 bits key size and RSA algorithm is the only choice that is backwards-compatible all the way to OS 10.4 Tiger systems. You will now be asked to approve Key Pair Information. Note that all this information becomes part of the certificate you’ll be sharing with the outer world. They may be filled out frivolously, though if the certificate might ever be used for other purposes or on non-Apple systems, there might be cases of failure if certain fields do not match reality (or at least expectations). The other items are optional. After a decade of improper defaults, Apple finally fixed the default settings in this pane. Details for this extension are discussed on the separate page X.509 v3 Certificate Extensions. Next you’ll be offered the Key Usage Extension settings. If highest compatibility with all systems Apple and otherwise is your priority, stay with Apple’s default choice of the RSA algorithm and 2048 bits. That page details your options in an all-Mac environment, broken out by how far back in terms of Mail/Mac OS versions you wish to support. Findings during testing of these options incited me to make a new in 2018 separate page discussing key size and algorithms. Mugen download 11It is OK to include it if you want, or disable it if you want—both ways work, in my testing. Next you’ll be hit with the Extended Key Usage Extension settings:This one’s defaults are OK. Once you’ve made your selection(s), click Continue. That experimentation is totally on you □. In theory it’s possible to add more if you want one certificate to serve other functions. If you wish for your certificate to work on all versions of OS X/macOS and Apple Mail versions from Mojave back to 10.4 Tiger/Mail 2, you must ensure that the following 4 items are checked:All my testing involves these selections only.
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