Force sidebar height 100% using CSS (with a sticky bottom image)?

I've been banging my head against the wall for hours trying to figure out this issue and think it must be something small I'm missing. I've searched online, but nothing I have found seems to work. The HTML is:

<body>
  <div id="header">
    <div id="bannerleft">
    </div>

    <div id="bannerright">
      <div id="WebLinks">
        <span>Web Links:</span>
        <ul>
          <li><a href="#"><img src="../../Content/images/MySpace_32x32.png" alt="MySpace"/></a></li>
          <li><a href="#"><img src="../../Content/images/FaceBook_32x32.png" alt="Facebook"/></a></li>
          <li><a href="#"><img src="../../Content/images/Youtube_32x32.png" alt="YouTube"/></a></li>
        </ul>
      </div>
    </div>
  </div>
  <div id="Sidebar">
    <div id="SidebarBottom">
    </div>
  </div>
  <div id="NavigationContainer">
    <ul id="Navigation">
      <li><a href="#">Nav</a></li>
      <li><a href="#">Nav</a></li>
      <li><a href="#">Nav</a></li>
      <li><a href="#">Nav</a></li>
      <li><a href="#">Nav</a></li>
      <li><a href="#">Nav</a></li>
    </ul>
  </div>
  <div id="Main">
    <!-- content -->
  </div>
</body>

My full CSS is:

* {
  margin: 0px;
  padding: 0px;
}

body {
  font-family: Calibri, Sans-Serif;
  height: 100%;
}

#header {
  width: 100%;
  z-index: 1;
  height: 340px;
  background-image: url("../../Content/images/bannercenter.gif");
  background-repeat: repeat-x;
}

#header #bannerleft {
  float: left;
  background-image: url("../../Content/images/bannerleft.gif");
  background-repeat: no-repeat;
  height: 340px;
  width: 439px;
  z-index: 2;
}

#bannerright {
  float: right;
  background-image: url("../../Content/images/bannerright.gif");
  background-repeat: no-repeat;
  width: 382px;
  height: 340px;
  background-color: White;
  z-index: 2;
}

#Sidebar {
  width: 180px;
  background: url("../../Content/images/Sidebar.png") repeat-y;
  z-index: 2;
  height: 100%;
  position: absolute;
}

#SidebarBottom {
  margin-left: 33px;
  height: 100%;
  background: url("../../Content/images/SidebarImage.png") no-repeat bottom;
}

#NavigationContainer {
  position: absolute;
  top: 350px;
  width: 100%;
  background-color: #bbc4c3;
  height: 29px;
  z-index: 1;
  left: 0px;
}

#Navigation {
  margin-left: 190px;
  font-family: Calibri, Sans-Serif;
}

#Navigation li {
  float: left;
  list-style: none;
  padding-right: 3%;
  padding-top: 6px;
  font-size: 100%;
}

#Navigation a:link, a:active, a:visited {
  color: #012235;
  text-decoration: none;
  font-weight: 500;
}

#Navigation a:hover {
  color: White;
}

#WebLinks {
  float: right;
  color: #00324b;
  margin-top: 50px;
  width: 375px;
}

#WebLinks span {
  float: left;
  margin-right: 7px;
  margin-left: 21px;
  font-size: 10pt;
  margin-top: 8px;
  font-family: Helvetica;
}

#WebLinks ul li {
  float: left;
  padding-right: 7px;
  list-style: none;
}

#WebLinks ul li a {
  text-decoration: none;
  font-size: 8pt;
  color: #00324b;
  font-weight: normal;
}

#WebLinks ul li a img {
  border-style: none;
}

#WebLinks ul li a:hover {
  color: #bcc5c4;
}

I'd like the sidebar to stretch in height with the content of my page and leave the sidebar bottom image always at the bottom of the sidebar.

This worked for me

.container { 
  overflow: hidden; 
  .... 
} 

#sidebar { 
  margin-bottom: -5000px; /* any large number will do */
  padding-bottom: 5000px; 
  .... 
}

Until CSS's flexbox becomes more mainstream, you can always just absolutely position the sidebar, sticking it zero pixels away from the top and bottom, then set a margin on your main container to compensate.

JSFiddle

http://jsfiddle.net/QDCGv/

HTML

<section class="sidebar">I'm a sidebar.</section>

<section class="main">I'm the main section.</section>

CSS

section.sidebar {
  width: 250px;
  position: absolute;
  top: 0;
  bottom: 0;
  background-color: green;
}

section.main { margin-left: 250px; }

Note: This is an über simple way to do this but you'll find bottom does not mean "bottom of page," but "bottom of window." The sidebar will probably abrubtly end if your main content scrolls down.

UPDATE: As this answer is still getting votes both up and down, and is at the time of writing eight years old: There are probably better techniques out there now. Original answer follows below.

Clearly you are looking for the Faux columns technique :-)

By how the height-property is calculated, you can't set height: 100% inside something that has auto-height.

I would use css tables to achieve a 100% sidebar height.

The basic idea is to wrap the sidebar and main divs in a container.

Give the container a display:table

And give the 2 child divs (sidebar and main) a display: table-cell

Like so..

#container {
display: table;
}
#main {
display: table-cell;
vertical-align: top;
}
#sidebar {
display: table-cell;
vertical-align: top;
}

Take a look at this LIVE DEMO where I have modified your initial markup using the above technique (I have used background colors for the different divs so that you can see which ones are which)

Flexbox (http://caniuse.com/#feat=flexbox)

First wrap the columns you want in a div or section, ex:

<div class="content">
    <div class="main"></div>
    <div class="sidebar"></div>
</div>

Then add the following CSS:

.content {
    display: -webkit-box;
    display: -moz-box;
    display: -ms-flexbox;
    display: -webkit-flex;
    display: flex;
}

Force sidebar height 100% using CSS (with a sticky bottom image)?

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