[FoRK] GPG/PGP for MS-Outlook - Suspicious absence of options

Frank Bergman (fraber) fraber at fraber.de
Mon Jul 1 09:53:46 PDT 2013

Does somebody have a reasonable statistic on the market
share of different email clients (including the Web variants)?
Any idea how to organize key exchange for not-so-IT-savvy
people across these systems?
And yes, I also tried to push Linux on the desktop, until we hit
OpenOffice Impress. It sucks so bad that everybody in our little
open-source company is now back to MS-Office...


From: Stephen D. Williams [mailto:sdw at lig.net] 
Sent: Monday, July 01, 2013 6:40 PM
To: Friends of Rohit Khare
Cc: Frank Bergman (fraber)
Subject: Re: [FoRK] GPG/PGP for MS-Outlook - Suspicious absence of options

How can you use Outlook for anything serious?  It is a broken toy of an
email client.  And Exchange!  Expensive, resource hog, fragile email storage
(I've heard corruption horror stories for years).

When used with Office365.com email service, even calendaring barely works.
Something basic like "share my calendar with the company" doesn't exist.
Quite a bad contrast with Gmail.  I'm perfectly fine with using a web
interface for all calendar editing, receiving email alerts with working URLs
(something Exchange/Office365 has trouble with).  There's no fundamental
reason that calendaring and email have to be combined and intermingled.

For GPG integration, how about:
Calendaring can be added on, with easy support for Gmail, plugin support for
Exchange style, and a number of open source and commercial calendar servers.

Recently I considered non-Exchange self-hosted email / calendar
alternatives.  Standard open source solutions completely solve the MTA
(Postfix, perhaps sendmail), Imap4 (dovecot, etc.), and email client
(Thunderbird, Roundcube for web email).  It appears that Bedework will
probably be the leading calendar server, however it isn't a standard
installed thing yet.

This product nicely leverages standard Linux email systems, ties it all
together with installation and management, and adds proprietary calendar
support, with available Outlook integration.  They have a free package
without Outlook integration, pay with it, which is a nice enough split.

<http://www.blue-mind.net/spip.php?page=sommaire&lang=en> &lang=en

For calendaring components, I narrowed down to these:

For a completely free email / calendar stack, except probably for anti-spam
service, I put together this recently as a tentative list:

Given a Linux VM, installing a local email server on Linux:

1.	SMTP / Imap4 configuration: 1-2 hours.

2.	Webmail: 1 hour. 

3.	Calendar server: 1-4 hours.  Or use web calendaring service with no
setup time.

4.	Best Anti-spam install: 1-2 hours.  $0-1000

5.	Reliable backup (via rsync to a spare local directory plus remote to
another server): 1 hour.

Some anti-spam options are free, others cost up to $1000/yr. and are easier
to install.
Once installed, the VM can be imaged to prevent ever needing reinstall.

Scalable, easily backed up, and secure email on Linux is trivial: Postfix
(MTA) + Dovecot (Imap4+indexing) is easy to install, can use any amount of
storage, and because of intelligent Imap4 indexing, handles tens of
thousands of messages per folder and thousands of folders easily for any
Imap4 client.  I have always found it to be faster than Exchange servers.

Roundcube seems to be the best web mail client:

Anti-spam, virus scanning, phishing defeat can be handled by free and
commercial systems, some of which are listed below.  A complete service can
be had for $1000/yr. including a prebuilt VM that is easy to insert.

Bedework appears to be the widely used and ideal calendar server software.
Note that it seems to have far more features and be far more flexible than
Exchange for calendaring activities.

Used by Berkeley and many others:

For those that insist on using Outlook, this plugin, at $23 per license,
supports calendar integration in Outlook for all of these calendar sources:
Supported are (alphabetical):
AllConnected4, Atmail2, Baikal12, Bedework1, Citadel12,
Chandler Cosmo1, Communigate Pro1, Darwin CalendarServer12, DAViCal12,
EPL12, EGroupware12, Fruux12, Google
Calendar & Tasks1, Gmail
<http://ical.gutentag.ch/forum/viewtopic.php?id=42> Contacts2, GroupOffice
Prof12, Horde12, IceWarp12, iCloud
> 12, Infomaniak <http://ical.gutentag.ch/forum/viewtopic.php?id=501> 12,
Kerio12, maXvis2, Office2s, OpenXchange2, Oracle Convergence, Owncloud(1)2,
Posteo2, Scalix, SmarterMail2, SnapAppointments, SOGo12, Synology,
Terminland.de, Tine <http://ical.gutentag.ch/forum/viewtopic.php?id=459> 2,
Tobit David.fx-Server 11, WebCalendar (only 1.05), Yahoo12, Zarafa1 and

Why wouldn't we use Exchange Server?

1.	Slow 

2.	Unreliable 

3.	Tends to lead to limited storage, probably due to using a relational
database for email storage. 

4.	Non-standard email and some mangling of messages. 

5.	Difficult to backup, restore, and recover from problems.  Probably
requires an expensive add-on for proper backup.

6.	Requires a lot of effort to install and maintain. 

7.	Expense for server, client licenses, and related services. 

8.	Have to run on a Windows server rather than Linux.  This requires
another expensive license, more installation and maintenance time, requires
time consuming OS updates and maintenance, etc. 


On 7/1/13 8:29 AM, Frank Bergman (fraber) wrote:


Did you ever try to install PGP/GPG on Windows Outlook?

There are only very limited options (see below). I'm 

not a big fan of conspiracy theories, but I can't 

imagine that there is no market for that, particularly 

given the ease of creating an Outlook plug-in that 

communicates with GPG...

Here is what I found:

- PGP got bought by Symantec, they don't release the

  source code anymore (NSA backdoor), and the purchasing

  page is currently broken on their Web site

  (Symantec Internal Error Page! An Internal Exception 

  has occurred. Please contact Administrator.)

- GPG exists, but is very GNU (GNU's Not User-friendly)

- There are several Outlook plug-ins, but none of 

  them worked for me. At least you can say they

  don't receive a lot of attention:

	- G-Data (abandoned since 2009)

	- gpg4win.de (German only, hangs with my Outlook)

	- GPGol (buggy, didn't work for me)

This mess contrasts with the relative ease of developing 

Outlook plug-ins. I believe there is a great opportunity 

to develop a software free for private use software that 

would require a license for professional use. Maybe the 

developers could make key management a bit easier by 

providing "half secure" features or "default scenarios" 

(like Ruby - convention over configuration) like 

automatically importing keys from friends or similar. 

Sure, that's not 100.000% secure, but 99.999% is better

than sending out unencrypted stuff...

I'll be happy to help with writing the business plan 

and with experience running low-budget start-ups :-)

PR expenses will be close to zero in the current

environment of public outrage in Europe and other parts

of the world, where even mass-media would write about

any reasonable product. And marketing could be completely 

viral if the system sends out mails with a viral footer 

inviting the receiver to download and install the system.




Frank Bergmann

Dipl.-Ing., MBA

Founder ]project-open[

Tel: +34 933 250 914

Cell: +34 609 953 751

Fax: +34 932 890 729







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