diff --git a/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/AutocompleteContainer.js b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/AutocompleteContainer.js
index a9711ece..5cb885ac 100644
--- a/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/AutocompleteContainer.js
+++ b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/AutocompleteContainer.js
@@ -5,6 +5,7 @@ import clickOutside from 'react-click-outside';
 import AutocompleteWidget from './AutocompleteWidget';
 import { getSlateEditor } from '../../utils';
 import { getAccents, getPosAfterEmphasis } from '../../slate/transforms';
+import { matchUnderCursor } from './utils';
 
 const escapeCode = 27;
 const arrowUpCode = 38;
@@ -170,7 +171,18 @@ class AutocompleteContainer extends PureComponent {
 
       if (extension && item) {
         const change = state.change();
-        change.deleteBackward(term.length).insertText(extension.markdownText(item, term)).focus();
+
+        const text = change.anchorText.text
+        const cursor = change.anchorOffset;
+
+        const { start, end } = matchUnderCursor({ text, cursor, regexp: extension.termRegex });
+
+        change.
+          deleteBackward(cursor - start).
+          deleteForward(end - cursor).
+          insertText(extension.markdownText(item, term)).
+          focus();
+
         this.props.onChange(change.state, true);
       }
 
diff --git a/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.js b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.js
new file mode 100644
index 00000000..d8cb7067
--- /dev/null
+++ b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.js
@@ -0,0 +1,20 @@
+export const matchUnderCursor = ({ text, regexp, cursor }) => {
+  const result = {
+    match: '',
+    start: cursor,
+    end: cursor
+  }
+
+  for (let start = cursor; start >= 0; start--) {
+    for (let end = cursor; end <= text.length; end++) {
+      const chunk = text.slice(start, end);
+      if (regexp.test(chunk) && chunk.length > result.match.length) {
+        result.match = chunk;
+        result.start = start;
+        result.end = end;
+      }
+    }
+  }
+
+  return result;
+}
diff --git a/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.spec.js b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.spec.js
new file mode 100644
index 00000000..7c0a977b
--- /dev/null
+++ b/src/client/components/PlainMarkdownInput/plugins/slate-autocomplete-plugin/utils.spec.js
@@ -0,0 +1,42 @@
+import { expect } from 'chai';
+
+import { matchUnderCursor } from './utils';
+
+describe('matchUnderCursor', () => {
+  it('should find regexp match under cursor', () => {
+    const regexp = /^\$(\w*)$/;
+
+    const tests = [
+      // returns match under cursor
+      {
+        args: { text: 'abc $def ghi $jkl mno', regexp, cursor: 5 },
+        want: { match: '$def', start: 4, end: 8 }
+      },
+      {
+        args: { text: 'abc $def ghi $jkl mno', regexp, cursor: 14 },
+        want: { match: '$jkl', start: 13, end: 17 }
+      },
+      // move cursor left to right to test all cases
+      ...('abc $def ghi'.split('').reduce((acc, ch, cursor) => {
+        return [
+          ...acc,
+          {
+            args: { text: 'abc $def ghi', regexp, cursor },
+            ...(
+              // if cursor is out of match then return empty match
+              (cursor < 4 || cursor > 8) ?
+                { want: { match: '', start: cursor, end: cursor } } :
+                // if cursor is on (or on edges of) match then return match and its boundaries
+                { want: { match: '$def', start: 4, end: 8 } }
+            )
+          }
+        ]
+      }, []))
+    ]
+
+    tests.forEach(({ args, want }) => {
+      const got = matchUnderCursor(args)
+      expect(got).to.deep.equal(want, `input: ${JSON.stringify(args)}`)
+    })
+  })
+})