diff --git a/server/api/hooks.js b/server/api/hooks.js
index 6afe7133..3c548f93 100644
--- a/server/api/hooks.js
+++ b/server/api/hooks.js
@@ -71,7 +71,7 @@ router.post('hooks.slack', async ctx => {
   if (results.length) {
     const attachments = [];
     for (const result of results) {
-      attachments.push(presentSlackAttachment(result.document));
+      attachments.push(presentSlackAttachment(result.document, result.context));
     }
 
     ctx.body = {
diff --git a/server/api/hooks.test.js b/server/api/hooks.test.js
index 3fc9b36f..14ab1bca 100644
--- a/server/api/hooks.test.js
+++ b/server/api/hooks.test.js
@@ -3,6 +3,7 @@ import TestServer from 'fetch-test-server';
 import app from '..';
 import { Authentication } from '../models';
 import { flushdb, seed } from '../test/support';
+import { buildDocument } from '../test/factories';
 import * as Slack from '../slack';
 
 const server = new TestServer(app.callback());
@@ -65,19 +66,26 @@ describe('#hooks.slack', async () => {
   });
 
   it('should return search results', async () => {
-    const { user, document, collection } = await seed();
-
+    const { user, collection } = await seed();
+    const document = await buildDocument({
+      title: 'This title contains a search term',
+      userId: user.id,
+      teamId: user.teamId,
+    });
     const res = await server.post('/api/hooks.slack', {
       body: {
         token: process.env.SLACK_VERIFICATION_TOKEN,
         user_id: user.serviceId,
-        text: document.title,
+        text: 'contains',
       },
     });
     const body = await res.json();
     expect(res.status).toEqual(200);
     expect(body.attachments.length).toEqual(1);
     expect(body.attachments[0].title).toEqual(document.title);
+    expect(body.attachments[0].text).toEqual(
+      'This title *contains* a search term'
+    );
     expect(body.attachments[0].footer).toEqual(collection.name);
   });
 
diff --git a/server/models/Document.js b/server/models/Document.js
index ff605c2d..de17335d 100644
--- a/server/models/Document.js
+++ b/server/models/Document.js
@@ -208,7 +208,7 @@ Document.searchForUser = async (
     SELECT
       id,
       ts_rank(documents."searchVector", plainto_tsquery('english', :query)) as "searchRanking",
-      ts_headline('english', "text", plainto_tsquery('english', :query), 'MaxFragments=1, MinWords=20, MaxWords=35') as "searchContext"
+      ts_headline('english', "text", plainto_tsquery('english', :query), 'MaxFragments=1, MinWords=20, MaxWords=30') as "searchContext"
     FROM documents
     WHERE "searchVector" @@ plainto_tsquery('english', :query) AND
       "teamId" = '${user.teamId}'::uuid AND
diff --git a/server/presenters/slackAttachment.js b/server/presenters/slackAttachment.js
index d1f7c9f0..2917ffd2 100644
--- a/server/presenters/slackAttachment.js
+++ b/server/presenters/slackAttachment.js
@@ -1,13 +1,17 @@
 // @flow
 import { Document } from '../models';
 
-function present(document: Document) {
+function present(document: Document, context?: string) {
+  // the context contains <b> tags around search terms, we convert them here
+  // to the markdown format that slack expects to receive.
+  const text = context ? context.replace(/<\/?b>/, '*') : document.getSummary();
+
   return {
     color: document.collection.color,
     title: document.title,
     title_link: `${process.env.URL}${document.getUrl()}`,
     footer: document.collection.name,
-    text: document.getSummary(),
+    text,
     ts: document.getTimestamp(),
   };
 }