diff --git a/web/src/css/header.less b/web/src/css/header.less
index 4813b9333..90907ec78 100644
--- a/web/src/css/header.less
+++ b/web/src/css/header.less
@@ -1,24 +1,66 @@
 @import (reference) '../../node_modules/bootstrap/less/variables.less';
 @import (reference) '../../node_modules/bootstrap/less/mixins/grid.less';
 
+@menu-height: 85px;
+
+
 header {
-    padding-top: 0.5em;
+    padding-top: 6px;
     background-color: white;
     @separator-color: lighten(grey, 15%);
-    .menu {
-        padding: 10px;
+    menu {
+        display: block;
+        margin: 0;
+        padding: 0;
         border-bottom: solid @separator-color 1px;
+        height: @menu-height;
+        overflow: visible; // search help context laps over.
     }
 }
 
-@menu-row-gutter-width: 5px;
-.menu-row {
-    .make-row(@menu-row-gutter-width);
+.menu-group {
+    @description-height: 16px;
+    display: inline-block;
+    height: @menu-height;
+    vertical-align: top;
+
+    .entry {
+        height: (@menu-height - @description-height)/3;
+        line-height: 1;
+        padding: 0.5rem 1rem;
+
+        label {
+            font-size: 1.2rem;
+            font-weight: normal;
+            margin: 0;
+        }
+        input[type=checkbox] {
+            margin: 0 2px;
+            vertical-align: middle;
+        }
+    }
+    .description {
+        height: @description-height;
+        text-align: center;
+        font-size: 0.9rem;
+    }
+}
+.menu-group + .menu-group:before {
+    @space: 10px;
+    content: " ";
+    border-left: solid 1px lighten(grey, 40%);
+    margin-top: @space;
+    height: @menu-height - @space*2;
+    position: absolute;
+}
+
+@menu-main-gutter-width: 5px;
+.menu-main {
+    .make-row(@menu-main-gutter-width);
 }
 
 .filter-input {
-    .make-sm-column(3, @menu-row-gutter-width);
-    margin-bottom:5px;
+    .make-sm-column(4, @menu-main-gutter-width);
 }
 
 .filter-input .popover {
diff --git a/web/src/js/components/FlowView/ToggleEdit.jsx b/web/src/js/components/FlowView/ToggleEdit.jsx
index 9016348e4..6a691a3d3 100644
--- a/web/src/js/components/FlowView/ToggleEdit.jsx
+++ b/web/src/js/components/FlowView/ToggleEdit.jsx
@@ -14,11 +14,11 @@ function ToggleEdit({ isEdit, startEdit, stopEdit, flow, modifiedFlow }) {
     return (
         <div className="edit-flow-container">
             {isEdit ?
-                <a className="edit-flow" onClick={() => stopEdit(flow, modifiedFlow)}>
+                <a className="edit-flow" title="Finish Edit" onClick={() => stopEdit(flow, modifiedFlow)}>
                     <i className="fa fa-check"/>
                 </a>
                 :
-                <a className="edit-flow" onClick={() => startEdit(flow)}>
+                <a className="edit-flow" title="Edit Flow" onClick={() => startEdit(flow)}>
                     <i className="fa fa-pencil"/>
                 </a>
             }
diff --git a/web/src/js/components/Header.jsx b/web/src/js/components/Header.jsx
index 702786e6b..1500db1ba 100644
--- a/web/src/js/components/Header.jsx
+++ b/web/src/js/components/Header.jsx
@@ -2,14 +2,13 @@ import React, { Component, PropTypes } from 'react'
 import { connect } from 'react-redux'
 import classnames from 'classnames'
 import MainMenu from './Header/MainMenu'
-import ViewMenu from './Header/ViewMenu'
 import OptionMenu from './Header/OptionMenu'
 import FileMenu from './Header/FileMenu'
 import FlowMenu from './Header/FlowMenu'
 import {setActiveMenu} from '../ducks/ui/header'
 
 class Header extends Component {
-    static entries = [MainMenu, ViewMenu, OptionMenu]
+    static entries = [MainMenu, OptionMenu]
 
     handleClick(active, e) {
         e.preventDefault()
@@ -38,9 +37,9 @@ class Header extends Component {
                         </a>
                     ))}
                 </nav>
-                <div className="menu">
+                <menu>
                     <Active/>
-                </div>
+                </menu>
             </header>
         )
     }
diff --git a/web/src/js/components/Header/FlowMenu.jsx b/web/src/js/components/Header/FlowMenu.jsx
index e78a49aa8..e0c59afeb 100644
--- a/web/src/js/components/Header/FlowMenu.jsx
+++ b/web/src/js/components/Header/FlowMenu.jsx
@@ -18,15 +18,12 @@ FlowMenu.propTypes = {
 function FlowMenu({ flow, acceptFlow, replayFlow, duplicateFlow, removeFlow, revertFlow }) {
     return (
         <div>
-            <div className="menu-row">
-                <Button disabled={!flow || !flow.intercepted} title="[a]ccept intercepted flow" text="Accept" icon="fa-play" onClick={() => acceptFlow(flow)} />
-                <Button title="[r]eplay flow" text="Replay" icon="fa-repeat" onClick={() => replayFlow(flow)} />
-                <Button title="[D]uplicate flow" text="Duplicate" icon="fa-copy" onClick={() => duplicateFlow(flow)} />
-                <Button title="[d]elete flow" text="Delete" icon="fa-trash" onClick={() => removeFlow(flow)}/>
-                <Button disabled={!flow || !flow.modified} title="revert changes to flow [V]" text="Revert" icon="fa-history" onClick={() => revertFlow(flow)} />
-                <Button title="download" text="Download" icon="fa-download" onClick={() => window.location = MessageUtils.getContentURL(flow, flow.response)}/>
-            </div>
-            <div className="clearfix"/>
+            <Button disabled={!flow || !flow.intercepted} title="[a]ccept intercepted flow" text="Accept" icon="fa-play" onClick={() => acceptFlow(flow)} />
+            <Button title="[r]eplay flow" text="Replay" icon="fa-repeat" onClick={() => replayFlow(flow)} />
+            <Button title="[D]uplicate flow" text="Duplicate" icon="fa-copy" onClick={() => duplicateFlow(flow)} />
+            <Button title="[d]elete flow" text="Delete" icon="fa-trash" onClick={() => removeFlow(flow)}/>
+            <Button disabled={!flow || !flow.modified} title="revert changes to flow [V]" text="Revert" icon="fa-history" onClick={() => revertFlow(flow)} />
+            <Button title="download" text="Download" icon="fa-download" onClick={() => window.location = MessageUtils.getContentURL(flow, flow.response)}/>
         </div>
     )
 }
diff --git a/web/src/js/components/Header/MainMenu.jsx b/web/src/js/components/Header/MainMenu.jsx
index 5ab3fa9d9..6a4e12bff 100644
--- a/web/src/js/components/Header/MainMenu.jsx
+++ b/web/src/js/components/Header/MainMenu.jsx
@@ -1,20 +1,17 @@
-import React, { Component, PropTypes } from 'react'
-import { connect } from 'react-redux'
-import FilterInput from './FilterInput'
-import { update as updateSettings } from '../../ducks/settings'
-import { setFilter, setHighlight } from '../../ducks/flows'
+import React, { Component, PropTypes } from "react"
+import { connect } from "react-redux"
+import FilterInput from "./FilterInput"
+import { update as updateSettings } from "../../ducks/settings"
+import { setFilter, setHighlight } from "../../ducks/flows"
 
 MainMenu.title = "Start"
 
 export default function MainMenu() {
     return (
-        <div>
-            <div className="menu-row">
-                <FlowFilterInput/>
-                <HighlightInput/>
-                <InterceptInput/>
-            </div>
-            <div className="clearfix"></div>
+        <div className="menu-main">
+            <FlowFilterInput/>
+            <HighlightInput/>
+            <InterceptInput/>
         </div>
     )
 }
diff --git a/web/src/js/components/Header/MenuToggle.jsx b/web/src/js/components/Header/MenuToggle.jsx
new file mode 100644
index 000000000..726db7bd1
--- /dev/null
+++ b/web/src/js/components/Header/MenuToggle.jsx
@@ -0,0 +1,69 @@
+import { PropTypes } from "react"
+import { connect } from "react-redux"
+import { update as updateSettings } from "../../ducks/settings"
+import { toggleVisibility } from "../../ducks/eventLog"
+
+MenuToggle.propTypes = {
+    value: PropTypes.bool.isRequired,
+    onChange: PropTypes.func.isRequired,
+    children: PropTypes.node.isRequired,
+}
+
+export function MenuToggle({ value, onChange, children }) {
+    return (
+        <div className="entry">
+            <label>
+                <input type="checkbox"
+                       value={value}
+                       onChange={onChange}/>
+                {children}
+            </label>
+        </div>
+    )
+}
+
+
+SettingsToggle.propTypes = {
+    setting: PropTypes.string.isRequired,
+    children: PropTypes.node.isRequired,
+}
+
+export function SettingsToggle({ setting, children, settings, updateSettings }) {
+    return (
+        <MenuToggle
+            value={settings[setting] || false} // we don't have settings initially, so just pass false.
+            onChange={() => updateSettings({ [setting]: !settings[setting] })}
+        >
+            {children}
+        </MenuToggle>
+    )
+}
+SettingsToggle = connect(
+    state => ({
+        settings: state.settings,
+    }),
+    {
+        updateSettings,
+    }
+)(SettingsToggle)
+
+
+export function EventlogToggle({ toggleVisibility, eventLogVisible }) {
+    return (
+        <MenuToggle
+            value={eventLogVisible}
+            onChange={toggleVisibility}
+        >
+            Display Event Log
+        </MenuToggle>
+    )
+}
+EventlogToggle = connect(
+    state => ({
+        eventLogVisible: state.eventLog.visible,
+    }),
+    {
+        toggleVisibility,
+    }
+)(EventlogToggle)
+
diff --git a/web/src/js/components/Header/OptionMenu.jsx b/web/src/js/components/Header/OptionMenu.jsx
index f1d19f48f..4fb5dc1f9 100644
--- a/web/src/js/components/Header/OptionMenu.jsx
+++ b/web/src/js/components/Header/OptionMenu.jsx
@@ -1,75 +1,59 @@
 import React, { PropTypes } from 'react'
 import { connect } from 'react-redux'
-import ToggleButton from '../common/ToggleButton'
-import ToggleInputButton from '../common/ToggleInputButton'
-import { update as updateSettings } from '../../ducks/settings'
+import {SettingsToggle, EventlogToggle} from './MenuToggle'
+import DocsLink from '../common/DocsLink'
 
 OptionMenu.title = 'Options'
 
-OptionMenu.propTypes = {
-    settings: PropTypes.object.isRequired,
-    updateSettings: PropTypes.func.isRequired,
-}
-
-function OptionMenu({ settings, updateSettings }) {
+export default function OptionMenu() {
     return (
         <div>
-            <div className="menu-row">
-                <ToggleButton text="showhost"
-                    checked={settings.showhost}
-                    onToggle={() => updateSettings({ showhost: !settings.showhost })}
-                />
-                <ToggleButton text="no_upstream_cert"
-                    checked={settings.no_upstream_cert}
-                    onToggle={() => updateSettings({ no_upstream_cert: !settings.no_upstream_cert })}
-                />
-                <ToggleButton text="rawtcp"
-                    checked={settings.rawtcp}
-                    onToggle={() => updateSettings({ rawtcp: !settings.rawtcp })}
-                />
-                <ToggleButton text="http2"
-                    checked={settings.http2}
-                    onToggle={() => updateSettings({ http2: !settings.http2 })}
-                />
-                <ToggleButton text="websocket"
-                    checked={settings.websocket}
-                    onToggle={() => updateSettings({ websocket: !settings.websocket })}
-                />
-                <ToggleButton text="anticache"
-                    checked={settings.anticache}
-                    onToggle={() => updateSettings({ anticache: !settings.anticache })}
-                />
-                <ToggleButton text="anticomp"
-                    checked={settings.anticomp}
-                    onToggle={() => updateSettings({ anticomp: !settings.anticomp })}
-                />
-                <ToggleInputButton name="stickyauth" placeholder="Sticky auth filter"
-                    checked={!!settings.stickyauth}
-                    txt={settings.stickyauth}
-                    onToggleChanged={txt => updateSettings({ stickyauth: !settings.stickyauth ? txt : null })}
-                />
-                <ToggleInputButton name="stickycookie" placeholder="Sticky cookie filter"
-                    checked={!!settings.stickycookie}
-                    txt={settings.stickycookie}
-                    onToggleChanged={txt => updateSettings({ stickycookie: !settings.stickycookie ? txt : null })}
-                />
-                <ToggleInputButton name="stream_large_bodies" placeholder="stream..."
-                    checked={!!settings.stream_large_bodies}
-                    txt={settings.stream_large_bodies}
-                    inputType="number"
-                    onToggleChanged={txt => updateSettings({ stream_large_bodies: !settings.stream_large_bodies ? txt : null })}
-                />
+            <div className="menu-group">
+                <SettingsToggle setting="http2">HTTP/2.0</SettingsToggle>
+                <SettingsToggle setting="websocket">WebSockets</SettingsToggle>
+                <SettingsToggle setting="rawtcp">Raw TCP</SettingsToggle>
+                <div className="description">Protocol Support</div>
             </div>
-            <div className="clearfix"/>
+            <div className="menu-group">
+                <SettingsToggle setting="anticache">
+                    Disable Caching <DocsLink resource="features/anticache.html"/>
+                </SettingsToggle>
+                <SettingsToggle setting="anticomp">
+                    Disable Compression <i className="fa fa-question-circle" title="Do not forward Accept-Encoding headers to the server to force an uncompressed response."></i>
+                </SettingsToggle>
+                <div className="entry"/>
+                <div className="description">HTTP Options</div>
+            </div>
+            <div className="menu-group">
+                <SettingsToggle setting="showhost">
+                    Use Host Header <i className="fa fa-question-circle" title="Use the Host header to construct URLs for display."></i>
+                </SettingsToggle>
+                <EventlogToggle/>
+                <div className="entry"/>
+                <div className="description">View Options</div>
+            </div>
+            { /*
+            <ToggleButton text="no_upstream_cert"
+                checked={settings.no_upstream_cert}
+                onToggle={() => updateSettings({ no_upstream_cert: !settings.no_upstream_cert })}
+            />
+            <ToggleInputButton name="stickyauth" placeholder="Sticky auth filter"
+                checked={!!settings.stickyauth}
+                txt={settings.stickyauth}
+                onToggleChanged={txt => updateSettings({ stickyauth: !settings.stickyauth ? txt : null })}
+            />
+            <ToggleInputButton name="stickycookie" placeholder="Sticky cookie filter"
+                checked={!!settings.stickycookie}
+                txt={settings.stickycookie}
+                onToggleChanged={txt => updateSettings({ stickycookie: !settings.stickycookie ? txt : null })}
+            />
+            <ToggleInputButton name="stream_large_bodies" placeholder="stream..."
+                checked={!!settings.stream_large_bodies}
+                txt={settings.stream_large_bodies}
+                inputType="number"
+                onToggleChanged={txt => updateSettings({ stream_large_bodies: !settings.stream_large_bodies ? txt : null })}
+            />
+            */}
         </div>
     )
 }
-
-export default connect(
-    state => ({
-        settings: state.settings,
-    }),
-    {
-        updateSettings,
-    }
-)(OptionMenu)
diff --git a/web/src/js/components/Header/ViewMenu.jsx b/web/src/js/components/Header/ViewMenu.jsx
deleted file mode 100644
index 22b370d15..000000000
--- a/web/src/js/components/Header/ViewMenu.jsx
+++ /dev/null
@@ -1,32 +0,0 @@
-import React, { PropTypes } from 'react'
-import { connect } from 'react-redux'
-import ToggleButton from '../common/ToggleButton'
-import { toggleVisibility } from '../../ducks/eventLog'
-
-ViewMenu.title = 'View'
-ViewMenu.route = 'flows'
-
-ViewMenu.propTypes = {
-    eventLogVisible: PropTypes.bool.isRequired,
-    toggleEventLog: PropTypes.func.isRequired,
-}
-
-function ViewMenu({ eventLogVisible, toggleEventLog }) {
-    return (
-        <div>
-            <div className="menu-row">
-                <ToggleButton text="Show Event Log" checked={eventLogVisible} onToggle={toggleEventLog} />
-            </div>
-            <div className="clearfix"></div>
-        </div>
-    )
-}
-
-export default connect(
-    state => ({
-        eventLogVisible: state.eventLog.visible,
-    }),
-    {
-        toggleEventLog: toggleVisibility,
-    }
-)(ViewMenu)
diff --git a/web/src/js/components/common/DocsLink.jsx b/web/src/js/components/common/DocsLink.jsx
new file mode 100644
index 000000000..182811a30
--- /dev/null
+++ b/web/src/js/components/common/DocsLink.jsx
@@ -0,0 +1,14 @@
+import { PropTypes } from 'react'
+
+DocsLink.propTypes = {
+    resource: PropTypes.string.isRequired,
+}
+
+export default function DocsLink({ children, resource }) {
+    let url = `http://docs.mitmproxy.org/en/stable/${resource}`
+    return (
+        <a target="_blank" href={url}>
+            {children || <i className="fa fa-question-circle"></i>}
+        </a>
+    )
+}
diff --git a/web/src/js/ducks/ui/header.js b/web/src/js/ducks/ui/header.js
index 25dfe6027..1eff3ef6d 100644
--- a/web/src/js/ducks/ui/header.js
+++ b/web/src/js/ducks/ui/header.js
@@ -4,7 +4,7 @@ export const SET_ACTIVE_MENU = 'UI_SET_ACTIVE_MENU'
 
 
 const defaultState = {
-    activeMenu: 'Start',
+    activeMenu: 'Options',
     isFlowSelected: false,
 }
 
@@ -22,7 +22,7 @@ export default function reducer(state = defaultState, action) {
             if (action.flowIds.length && !state.isFlowSelected) {
                 return {
                     ...state,
-                    activeMenu: 'Flow',
+                    activeMenu: 'Options',
                     isFlowSelected: true,
                 }
             }