Sent Messages or Sent – Getting Apple Mail and Spark to work together

For my iPhone I just love Readdle’s App called Spark. On MacOS I am still clinging to Apple Mail. Since all my Mail is stored on my Mac Mini MacOS server, I also work with server based folders. Here I noted a discrepancy between Apple Mail and Spark, because both programs use different presets for saving mail on the server. Fortunately I came across this websavers article, how to get both to work together smoothly.

Apple Mail Preferences

Apple Mail defaults to a sent mailbox/folder named „Sent Messages“. If the option to „Store sent messages on the server“ is active it will create a folder called „Sent Messages“ on the server and use that folder to save copies of sent messages. This conflicts with many other applications with use the folder „Sent“ instead.

Spark Default Preferences

As I am not yet on Sierra, the second part of the article did it for me:

  1. Select the „Sent“ folder on the server (in the folders pane on the left) by clicking on it once. It should *not* be at the top of the page next to Inbox/Drafts/Junk/etc, nor should it be under „Local Folders“ or „On My Mac“. It will be found under a heading indicating that it’s a server-side folder. For example, my heading says „Websavers“ as it’s my Websavers email account.
    If you do not see a server-side heading in the folder list or if you do and there is no Sent folder there then you must create a new folder by choosing the Mailbox menu, then „New Mailbox“. For the Location field, you must select the correct account to create it under, then set the name to „Sent“.
  2. Chose Mailbox from the system menu at the top of the screen
  3. Choose „Use this Mailbox as“ > and then choose „Sent Mailbox“.


Apple MacOS Server and iOS don’t like StartCom Certificates

An error reading „Cannot Connect Using SSL“ on my iPhone caused me some extra grey hair: The symptoms I observed since mid of December were:

  • iOS Mail came up with a SSL error when trying to negotiate SSL/TLS through the IMAP service on my MacOS server. Adding a new mailbox was not possible, Apple Mail always suggested to turn of SSL (which I didn’t want to do for good reason).
  • My Squirrelmail webbased email reader suddenly couldn’t connect to the IMAP mailbox anymore. The error observed was: „Error connecting to IMAP server: <server_name>. 0

First I thought that there was a problem with the MacOS Server, but when I switched to a self signed certificate – things worked OK again (only with the hint that I use an untrusted cert of course).

After some more googling around for the symptoms I observed, I came across this article Lists of available trusted root certificates in iOS (in German). It clearly mentions, that from December 2016 onward, the certificates of StartCom (which were available also cost free) are not recognized anymore. Now, my MacOS Server did not throw any error in the Server Manager, but the services didn’t work as expected anymore.

And for testing Squirrelmail, I found this very nice information at James Bottomley’s random Pages:

echo 'fsockopen("tls://yourmailserver.domain",993,$errno,$errmsg,15);'|php -a

I used it to check the connection to my mailserver, and look and behold, I got to see the PHP error that I had a certificate issue!

So I decided to order a RapidSSL certificate to replace the StartCom certificate. Said and done, set it all up, and voilá – all services are running smoothly again.

While the Server App correctly changes certs for all services including the postfix Mail service, I have configured TLS manually in the postfix as this was a requirement for my outbound mail forwarder. These configuration statements I always have to change manually when updating the certificate. Now there is at the end of the file:

smtp_tls_cert_file = /etc/certificates/<hostname>.ID.cert.pem
smtp_tls_CAfile = /etc/certificates/<hostname>.ID.chain.pem
smtp_tls_key_file = /etc/certificates/<hostname>.ID.key.pem

For the correct keys just compare to the statements before, like:

smtpd_tls_key_file = /etc/certificates/<hostname>.ID.key.pem
smtpd_tls_cert_file = /etc/certificates/<hostname>.ID.cert.pem

If you run into similar troubles as described above, I suggest to get a „real“ SSL certificate which is trusted by the Apple OS. I got mine from the folks at

iPhone 4 and Exchange calendar entries marked private

I just switched to an iPhone 4. From my poor old Nokia E72. Well, that is a real change! Since I work heavily with my calendar in Outlook, I wondered how I can set up the iPhone to sync with Exchange. The setup worked pretty flawless, but then I noticed I couldn’t create calendar entries marked as „private“.

It has to do with the concept of the calendar system. With the old Exchange – Outlook connection, there was one calendar and I was able to mark personal entries as „private“ to hide them from my colleagues who are allowed to look into my calendar for making appointments. My Nokia with Symbian allowed this setting of a private marker too.

The iPhone as well as Android software (as far as I know) do not know a private mark. Rather it is possible to set up several calendars. I learned, that I can subscribe to certain calendars online – for instance to show the week of the year or to show sunrise and sunset. 

That brought me to have a closer look at my Outlook (version 2010 by the way) and the Exchange server behind it (an Exchange 2007 serveR). Thus I found out, that on our company’s Exchange server I can create additional calendars.

So what I did now is the following:

– I created another calendar in my Outlook (on the Exchange server), named „Private“, to which my colleagues do not have access
– My Outlook 2010 allows me to show the „public“ calendar and the private calendar as an overlay, so I see all entries in one window
– my iPhone syncs perfectly with both calendars – so whenever I need to create a private entry I just choose it to go to the Exchange calendar named „private“, whereas a public entry goes to the regular Exchange calendar.

In this way I am able to work fine with my iPhone’s calendar system. Just a bit time needed to get used to it! 🙂 So, no need for any add-on! In any case, all googleing only led to the conclusion that marking a calendar entry as private is not possible with the iCal, nor is there any third party software which would offer that function (not even the well known pocket informant nor other similar software).

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