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- Backup or clone the disk first.<br />
Upgrade on the clone disk first.<br />
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- apply all updates to your current version of Ubuntu before you upgrade.<br />
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- Do not use ext4 if it prompt you.
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Here is the Ubuntu page on the upgrade: <a href="https://help.ubuntu.com/community/LucidUpgrades" rel="ugc">https://help.ubuntu.com/community/LucidUpgrades</a>&nbsp; Note that it says it's for Desktop upgrades as opposed to Server upgrades. &nbsp;There is a link to the release notes that tells about all the known broken things.<br />
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If this system is in daily use, you might want to hire an expert to do this upgrade.
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What should I expect to pay for an expert to do this upgrade? <br />
How much time should it take, in general?
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That's a good question, maybe some others can give you a better estimate based their own rates. &nbsp;Hourly consulting rates vary a great deal, maybe as low as $40 per hour to $200 per hour. &nbsp;If everything went perfectly, maybe as little as two hours but I would not expect things to go perfectly which is why I'm recommending you find someone experienced.<br />
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The first thing I would do is make a list of the softwares that you are using. &nbsp;Pay especial attention to any servers that you have running including SMB, web, and email. &nbsp;Then I would check to make sure they are included in the upgrade or find out what to do if they aren't. &nbsp;The servers probably have to be stopped while the upgrade is done.<br />
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I have an Ubuntu 8.04 server and I've decided that I'm going to put 10.04 on another machine instead of doing an upgrade. &nbsp;I installed 8.04 from a Live CD and then added all the servers and I don't think the upgrade will properly handle all that. &nbsp;Every recommendation I found suggested a clean install instead of an upgrade. &nbsp;And I have spare machine to put it on so that's what I will do. &nbsp;Soon. &nbsp;When I get to it...
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Check local IT consulting company for the expertise and price (then you don't need to pay travel and hotel fee).<br />
With hardware ready, it should be 1 day project (consulting company will not estimate 2 hours).<br />
I don't recommend pay by hour rate unless you know the person.<br />
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I agree that clean installation is better. However, for a non-experience staff, upgrade and play aside is the the learning chance. Once you get familiar with Linux world, then you can do a clean install and setup/migration.<br />
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Good luck. 
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Currently in place - Ubuntu 8.04.1, as a File Server (Samba)/Web/Mail<br />
Looking to upgrade to Ubuntu 10.4LTS<br />
<br />
I have given a cursory look at<br />
<a href="http://data-recovery-software-articles.blogspot.com/2010/05/how-to-upgrade-from-ubuntu-910-or-804.html" rel="ugc">http://data-recovery-software-articles.blogspot.com/2010/05/how-to-upgrade-from-ubuntu-910-or-804.html</a><br />
<br />
I have no Ubuntu experience, less installing it on a desktop. &nbsp;<br />
I have good knowledge of Microsoft Updates<br />
Is there anything that I should pay particular attention to/to watch out for?<br />
Server is RAID1
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Currently in place - Ubuntu 8.04.1, as a File Server (Samba)/Web/Mail
Looking to upgrade to Ubuntu 10.4LTS

I have given a cursory look at
http://data-recovery-software-articles.blogspot.com/2010/05/how-to-upgrade-from-ubuntu-910-or-804.html

I have no Ubuntu experience, less installing it on a desktop.  
I have good knowledge of Microsoft Updates
Is there anything that I should pay particular attention to/to watch out for?
Server is RAID1

Upgrade Ubuntu 8.04.1 to Ubuntu 10.4LTS potential issues

Linux is a UNIX-like open source operating system with hundreds of distinct distributions, including: Fedora, openSUSE, Ubuntu, Debian, Slackware, Gentoo, CentOS, and Arch Linux. Linux is generally associated with web and database servers, but has become popular in many niche industries and applications.