diff --git a/app/internal_packages/composer/styles/composer.less b/app/internal_packages/composer/styles/composer.less
index 8ab125433..c2a993817 100644
--- a/app/internal_packages/composer/styles/composer.less
+++ b/app/internal_packages/composer/styles/composer.less
@@ -33,6 +33,10 @@
   -webkit-margin-end: initial !important;
 }
 
+.RichEditor-root .link {
+  color: @text-color-link;
+  text-decoration: underline;
+}
 .RichEditor-root .custom-block-selected,
 .RichEditor-root .uneditable.custom-block-selected {
   border: 1px dashed @text-color;
@@ -143,11 +147,15 @@
     flex: 1;
     flex-shrink: 0;
     max-width: 32px;
+    text-align: center;
 
     .dropdown {
       padding: 5px;
       display: flex;
       flex-direction: row;
+      button {
+        max-width: 50px;
+      }
     }
   }
 }
diff --git a/app/src/components/composer-editor/link-plugins.jsx b/app/src/components/composer-editor/link-plugins.jsx
index 0d3035333..319e6ff5d 100644
--- a/app/src/components/composer-editor/link-plugins.jsx
+++ b/app/src/components/composer-editor/link-plugins.jsx
@@ -4,7 +4,7 @@ import { Mark } from 'slate';
 import AutoReplace from 'slate-auto-replace';
 import { RegExpUtils } from 'mailspring-exports';
 
-import { BuildMarkButtonWithValuePicker } from './toolbar-component-factories';
+import { BuildMarkButtonWithValuePicker, getMarkOfType } from './toolbar-component-factories';
 
 export const LINK_TYPE = 'link';
 
@@ -22,14 +22,28 @@ function onPaste(event, change, editor) {
   }
 }
 
-function renderMark({ mark, children }) {
-  if (mark.type === LINK_TYPE) {
-    const href = mark.data.href || mark.data.get('href');
+function renderMark({ mark, children, targetIsHTML }) {
+  if (mark.type !== LINK_TYPE) {
+    return;
+  }
+  const href = mark.data.href || mark.data.get('href');
+  if (targetIsHTML) {
     return (
       <a href={href} title={href}>
         {children}
       </a>
     );
+  } else {
+    const onClick = e => {
+      if (e.ctrlKey || e.metaKey) {
+        AppEnv.windowEventHandler.openLink({ href, metaKey: e.metaKey });
+      }
+    };
+    return (
+      <span className="link" title={href} onClick={onClick}>
+        {children}
+      </span>
+    );
   }
 }
 
@@ -66,12 +80,22 @@ export default [
       BuildMarkButtonWithValuePicker({
         type: LINK_TYPE,
         field: 'href',
-        iconClassOn: 'fa fa-unlink',
+        iconClassOn: 'fa fa-link',
         iconClassOff: 'fa fa-link',
         placeholder: 'http://',
       }),
     ],
     onPaste,
+    onKeyDown: function onKeyDown(event, change) {
+      // ensure space and enter always terminate links
+      if (!['Space', 'Enter', ' ', 'Return'].includes(event.key)) {
+        return;
+      }
+      const mark = getMarkOfType(change.value, LINK_TYPE);
+      if (mark) {
+        change.removeMark(mark);
+      }
+    },
     renderMark,
     rules,
     commands: {
diff --git a/app/src/components/composer-editor/toolbar-component-factories.jsx b/app/src/components/composer-editor/toolbar-component-factories.jsx
index b17320020..206646267 100644
--- a/app/src/components/composer-editor/toolbar-component-factories.jsx
+++ b/app/src/components/composer-editor/toolbar-component-factories.jsx
@@ -35,6 +35,33 @@ function removeMarksOfTypeInRange(change, range, type) {
   return change;
 }
 
+export function expandSelectionToRangeOfMark(change, type) {
+  const { selection, document } = change.value;
+  const node = document.getNode(selection.anchorKey);
+  let start = selection.anchorOffset;
+  let end = selection.anchorOffset;
+
+  // expand backwards until the mark disappears
+  while (start > 0 && node.getMarksAtIndex(start).find(m => m.type === type)) {
+    start -= 1;
+  }
+  // expand forwards until the mark disappears
+  while (end < node.text.length - 1 && node.getMarksAtIndex(end + 1).find(m => m.type === type)) {
+    end += 1;
+  }
+
+  // expand selection
+  change.select({
+    anchorKey: selection.anchorKey,
+    anchorOffset: start,
+    focusKey: selection.anchorKey,
+    focusOffset: end,
+    isFocused: true,
+    isBackward: false,
+  });
+  return change;
+}
+
 export function hasMark(value, type) {
   return !!getMarkOfType(value, type);
 }
@@ -107,7 +134,10 @@ export function BuildMarkButtonWithValuePicker(config) {
       const active = getMarkOfType(this.props.value, config.type);
       const fieldValue = (active && active.data.get(config.field)) || '';
       this.setState({ expanded: true, fieldValue: fieldValue }, () => {
-        setTimeout(() => this._inputEl.focus(), 0);
+        setTimeout(() => {
+          this._inputEl.focus();
+          this._inputEl.select();
+        }, 0);
       });
     };
 
@@ -117,6 +147,13 @@ export function BuildMarkButtonWithValuePicker(config) {
       // attach the URL value to the LINK that was created when we opened the link modal
       const { value, onChange } = this.props;
       const { fieldValue } = this.state;
+
+      if (fieldValue.trim() === '') {
+        this.onRemove(e);
+        this.setState({ expanded: false, fieldValue: '' });
+        return;
+      }
+
       const newMark = Mark.create({
         type: config.type,
         data: {
@@ -124,7 +161,17 @@ export function BuildMarkButtonWithValuePicker(config) {
         },
       });
 
-      if (value.selection.isCollapsed) {
+      const active = getMarkOfType(this.props.value, config.type);
+      if (active) {
+        // update the active mark
+        const change = value.change();
+        expandSelectionToRangeOfMark(change, config.type);
+        removeMarksOfTypeInRange(change, value.selection, config.type)
+          .addMark(newMark)
+          .focus();
+        onChange(change);
+      } else if (value.selection.isCollapsed) {
+        // apply new mark to new text
         onChange(
           value
             .change()
@@ -135,6 +182,7 @@ export function BuildMarkButtonWithValuePicker(config) {
             .focus()
         );
       } else {
+        // apply new mark to selected text
         onChange(
           removeMarksOfTypeInRange(value.change(), value.selection, config.type)
             .addMark(newMark)
@@ -175,7 +223,7 @@ export function BuildMarkButtonWithValuePicker(config) {
           onBlur={this.onBlur}
         >
           {active ? (
-            <button className="active" onMouseDown={this.onRemove}>
+            <button className="active" onMouseDown={this.onPrompt}>
               <i className={config.iconClassOn} />
             </button>
           ) : (
@@ -198,7 +246,7 @@ export function BuildMarkButtonWithValuePicker(config) {
                   }
                 }}
               />
-              <button onMouseDown={this.onConfirm}>Add</button>
+              <button onMouseDown={this.onConfirm}>{active ? 'Save' : 'Add'}</button>
             </div>
           )}
         </div>