diff --git a/CHANGELOG.md b/CHANGELOG.md
index 675c4b5bf240883fbb634520ef4ecb431a7dea5b..18dafa8e26747d1910484306adb828b7977b5a45 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,9 +5,14 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 
 ## [Unreleased]
 ## [Unreleased patch]
+
 ### Changed
 - Polls will be hidden with status content if "Collapse posts with subjects" is enabled and the post is collapsed.
 
+### Fixed
+- Autocomplete won't stop at the second @, so it'll still work with "@lain@l" and not start over.
+- Fixed weird autocomplete behavior when you write ":custom_emoji: ?"
+
 ## [2.1.0] - 2020-08-28
 ### Added
 - Autocomplete domains from list of known instances
diff --git a/src/services/completion/completion.js b/src/services/completion/completion.js
index df83d03d143f4ed20e4398f661306e03458b4d9a..8a6eba7e4d03dab635e0caf98bde67aa2633f71b 100644
--- a/src/services/completion/completion.js
+++ b/src/services/completion/completion.js
@@ -5,7 +5,7 @@ export const replaceWord = (str, toReplace, replacement) => {
 }
 
 export const wordAtPosition = (str, pos) => {
-  const words = splitIntoWords(str)
+  const words = splitByWhitespaceBoundary(str)
   const wordsWithPosition = addPositionToWords(words)
 
   return find(wordsWithPosition, ({ start, end }) => start <= pos && end > pos)
@@ -34,36 +34,36 @@ export const addPositionToWords = (words) => {
   }, [])
 }
 
-export const splitIntoWords = (str) => {
-  // Split at word boundaries
-  const regex = /\b/
-  const triggers = /[@#:]+$/
-
-  let split = str.split(regex)
-
-  // Add trailing @ and # to the following word.
-  const words = reduce(split, (result, word) => {
-    if (result.length > 0) {
-      let previous = result.pop()
-      const matches = previous.match(triggers)
-      if (matches) {
-        previous = previous.replace(triggers, '')
-        word = matches[0] + word
-      }
-      result.push(previous)
+export const splitByWhitespaceBoundary = (str) => {
+  let result = []
+  let currentWord = ''
+  for (let i = 0; i < str.length; i++) {
+    const currentChar = str[i]
+    // Starting a new word
+    if (!currentWord) {
+      currentWord = currentChar
+      continue
     }
-    result.push(word)
-
-    return result
-  }, [])
-
-  return words
+    // current character is whitespace while word isn't, or vice versa:
+    // add our current word to results, start over the current word.
+    if (!!currentChar.trim() !== !!currentWord.trim()) {
+      result.push(currentWord)
+      currentWord = currentChar
+      continue
+    }
+    currentWord += currentChar
+  }
+  // Add the last word we were working on
+  if (currentWord) {
+    result.push(currentWord)
+  }
+  return result
 }
 
 const completion = {
   wordAtPosition,
   addPositionToWords,
-  splitIntoWords,
+  splitByWhitespaceBoundary,
   replaceWord
 }
 
diff --git a/test/unit/specs/services/completion/completion.spec.js b/test/unit/specs/services/completion/completion.spec.js
index 8a41c6537ae9c02aee222b1cf5700fc838227639..81d3a26a2696e20a91cdc08e507274b7e7135c7b 100644
--- a/test/unit/specs/services/completion/completion.spec.js
+++ b/test/unit/specs/services/completion/completion.spec.js
@@ -1,8 +1,8 @@
-import { replaceWord, addPositionToWords, wordAtPosition, splitIntoWords } from '../../../../../src/services/completion/completion.js'
+import { replaceWord, addPositionToWords, wordAtPosition, splitByWhitespaceBoundary } from '../../../../../src/services/completion/completion.js'
 
 describe('addPositiontoWords', () => {
   it('adds the position to a word list', () => {
-    const words = ['hey', 'this', 'is', 'fun']
+    const words = ['hey', ' ', 'this', ' ', 'is', ' ', 'fun']
 
     const expected = [
       {
@@ -11,19 +11,34 @@ describe('addPositiontoWords', () => {
         end: 3
       },
       {
-        word: 'this',
+        word: ' ',
         start: 3,
-        end: 7
+        end: 4
       },
       {
-        word: 'is',
-        start: 7,
+        word: 'this',
+        start: 4,
+        end: 8
+      },
+      {
+        word: ' ',
+        start: 8,
         end: 9
       },
       {
-        word: 'fun',
+        word: 'is',
         start: 9,
+        end: 11
+      },
+      {
+        word: ' ',
+        start: 11,
         end: 12
+      },
+      {
+        word: 'fun',
+        start: 12,
+        end: 15
       }
     ]
 
@@ -33,11 +48,11 @@ describe('addPositiontoWords', () => {
   })
 })
 
-describe('splitIntoWords', () => {
+describe('splitByWhitespaceBoundary', () => {
   it('splits at whitespace boundaries', () => {
-    const str = 'This is a #nice @test for you, @idiot.'
-    const expected = ['This', ' ', 'is', ' ', 'a', ' ', '#nice', ' ', '@test', ' ', 'for', ' ', 'you', ', ', '@idiot', '.']
-    const res = splitIntoWords(str)
+    const str = 'This is a #nice @test for you,    @idiot@idiot.com'
+    const expected = ['This', ' ', 'is', ' ', 'a', ' ', '#nice', ' ', '@test', ' ', 'for', ' ', 'you,', '    ', '@idiot@idiot.com']
+    const res = splitByWhitespaceBoundary(str)
 
     expect(res).to.eql(expected)
   })
@@ -57,13 +72,13 @@ describe('wordAtPosition', () => {
 
 describe('replaceWord', () => {
   it('replaces a word (with start and end) with another word in a given string', () => {
-    const str = 'hey @take, how are you'
-    const wordsWithPosition = addPositionToWords(splitIntoWords(str))
+    const str = 'hey @take , how are you'
+    const wordsWithPosition = addPositionToWords(splitByWhitespaceBoundary(str))
     const toReplace = wordsWithPosition[2]
 
     expect(toReplace.word).to.eql('@take')
 
-    const expected = 'hey @takeshitakenji, how are you'
+    const expected = 'hey @takeshitakenji , how are you'
     const res = replaceWord(str, toReplace, '@takeshitakenji')
     expect(res).to.eql(expected)
   })