diff --git a/ts/components/StoryViewer.tsx b/ts/components/StoryViewer.tsx
index c451a455b..b7322abdc 100644
--- a/ts/components/StoryViewer.tsx
+++ b/ts/components/StoryViewer.tsx
@@ -44,9 +44,9 @@ import { ToastType } from '../state/ducks/toast';
 import { getAvatarColor } from '../types/Colors';
 import { getStoryBackground } from '../util/getStoryBackground';
 import { getStoryDuration } from '../util/getStoryDuration';
-import { graphemeAwareSlice } from '../util/graphemeAwareSlice';
 import type { saveAttachment } from '../util/saveAttachment';
 import { isVideoAttachment } from '../types/Attachment';
+import { graphemeAndLinkAwareSlice } from '../util/graphemeAndLinkAwareSlice';
 import { useEscapeHandling } from '../hooks/useEscapeHandling';
 import { useRetryStorySend } from '../hooks/useRetryStorySend';
 import { resolveStorySendStatus } from '../util/resolveStorySendStatus';
@@ -228,7 +228,7 @@ export function StoryViewer({
       return;
     }
 
-    return graphemeAwareSlice(
+    return graphemeAndLinkAwareSlice(
       attachment.caption,
       hasExpandedCaption ? CAPTION_MAX_LENGTH : CAPTION_INITIAL_LENGTH,
       CAPTION_BUFFER
diff --git a/ts/components/conversation/MessageBodyReadMore.tsx b/ts/components/conversation/MessageBodyReadMore.tsx
index b587e362d..8f2339b6b 100644
--- a/ts/components/conversation/MessageBodyReadMore.tsx
+++ b/ts/components/conversation/MessageBodyReadMore.tsx
@@ -5,7 +5,7 @@ import React from 'react';
 
 import type { Props as MessageBodyPropsType } from './MessageBody';
 import { MessageBody } from './MessageBody';
-import { graphemeAwareSlice } from '../../util/graphemeAwareSlice';
+import { graphemeAndLinkAwareSlice } from '../../util/graphemeAndLinkAwareSlice';
 
 export type Props = Pick<
   MessageBodyPropsType,
@@ -46,7 +46,7 @@ export function MessageBodyReadMore({
 }: Props): JSX.Element {
   const maxLength = displayLimit || INITIAL_LENGTH;
 
-  const { hasReadMore, text: slicedText } = graphemeAwareSlice(
+  const { hasReadMore, text: slicedText } = graphemeAndLinkAwareSlice(
     text,
     maxLength,
     BUFFER
diff --git a/ts/test-both/util/graphemeAndLinkAwareSlice.ts b/ts/test-both/util/graphemeAndLinkAwareSlice.ts
new file mode 100644
index 000000000..d27832b3b
--- /dev/null
+++ b/ts/test-both/util/graphemeAndLinkAwareSlice.ts
@@ -0,0 +1,70 @@
+// Copyright 2021 Signal Messenger, LLC
+// SPDX-License-Identifier: AGPL-3.0-only
+
+import { assert } from 'chai';
+import { graphemeAndLinkAwareSlice } from '../../util/graphemeAndLinkAwareSlice';
+
+describe('graphemeAndLinkAwareSlice', () => {
+  it('returns entire string when shorter than maximum', () => {
+    const shortString = 'Hello, Signal!';
+    const result = graphemeAndLinkAwareSlice(shortString, 50);
+
+    assert.strictEqual(result.text, shortString);
+    assert.isFalse(result.hasReadMore);
+  });
+
+  it('should return string longer than max but within buffer', () => {
+    const input = 'Hello, Signal!';
+    const result = graphemeAndLinkAwareSlice(input, 5, 10);
+
+    assert.strictEqual(result.text, input);
+    assert.isFalse(result.hasReadMore);
+  });
+
+  it('should include entire url and detect no more to read', () => {
+    const input = 'Hello, Signal! https://signal.org';
+    const result = graphemeAndLinkAwareSlice(input, 16, 0);
+
+    assert.strictEqual(result.text, input);
+    assert.isFalse(result.hasReadMore);
+  });
+
+  it('should include entire url and detect more to read', () => {
+    const input = 'Hello, Signal! https://signal.org additional text';
+    const inputProperlyTruncated = 'Hello, Signal! https://signal.org';
+
+    const result = graphemeAndLinkAwareSlice(input, 16, 0);
+    assert.strictEqual(result.text, inputProperlyTruncated);
+    assert.isTrue(result.hasReadMore);
+  });
+
+  it('should truncate normally when url present after truncation', () => {
+    const input = 'Hello, Signal! https://signal.org additional text';
+    const inputProperlyTruncated = 'Hello, Signal!';
+
+    const result = graphemeAndLinkAwareSlice(input, 14, 0);
+    assert.strictEqual(result.text, inputProperlyTruncated);
+    assert.isTrue(result.hasReadMore);
+  });
+
+  it('truncates after url when url present before and at truncation point', () => {
+    const input =
+      'Hello, Signal! https://signal.org additional text https://example.com/example more text';
+    const inputProperlyTruncated =
+      'Hello, Signal! https://signal.org additional text https://example.com/example';
+
+    const result = graphemeAndLinkAwareSlice(input, 55, 0);
+    assert.strictEqual(result.text, inputProperlyTruncated);
+    assert.isTrue(result.hasReadMore);
+  });
+
+  it('truncates after url when url present at and after truncation point', () => {
+    const input =
+      'Hello, Signal! https://signal.org additional text https://example.com/example more text';
+    const inputProperlyTruncated = 'Hello, Signal! https://signal.org';
+
+    const result = graphemeAndLinkAwareSlice(input, 26, 0);
+    assert.strictEqual(result.text, inputProperlyTruncated);
+    assert.isTrue(result.hasReadMore);
+  });
+});
diff --git a/ts/util/graphemeAndLinkAwareSlice.ts b/ts/util/graphemeAndLinkAwareSlice.ts
new file mode 100644
index 000000000..f5bd881d2
--- /dev/null
+++ b/ts/util/graphemeAndLinkAwareSlice.ts
@@ -0,0 +1,68 @@
+// Copyright 2021-2022 Signal Messenger, LLC
+// SPDX-License-Identifier: AGPL-3.0-only
+
+import LinkifyIt from 'linkify-it';
+
+export function graphemeAndLinkAwareSlice(
+  str: string,
+  length: number,
+  buffer = 100
+): {
+  hasReadMore: boolean;
+  text: string;
+} {
+  if (str.length <= length + buffer) {
+    return { text: str, hasReadMore: false };
+  }
+
+  let text: string | undefined;
+
+  for (const { index } of new Intl.Segmenter().segment(str)) {
+    if (!text && index >= length) {
+      text = str.slice(0, index);
+    }
+
+    if (text && index > length) {
+      text = expandToIncludeEntireLink(str, text);
+
+      return {
+        text,
+        hasReadMore: text.length < str.length,
+      };
+    }
+  }
+
+  return {
+    text: str,
+    hasReadMore: false,
+  };
+}
+
+const expandToIncludeEntireLink = (
+  original: string,
+  truncated: string
+): string => {
+  const linksInText = new LinkifyIt().match(original);
+
+  if (!linksInText) {
+    return truncated;
+  }
+
+  const invalidTruncationRanges: Array<LinkRange> = linksInText.map(
+    ({ index: startIndex, lastIndex }) => ({ startIndex, lastIndex })
+  );
+
+  const truncatedLink: Array<LinkRange> = invalidTruncationRanges.filter(
+    ({ startIndex, lastIndex }) =>
+      startIndex < truncated.length && lastIndex > truncated.length
+  );
+
+  if (truncatedLink.length === 0) return truncated;
+
+  return original.slice(0, truncatedLink[0].lastIndex);
+};
+
+type LinkRange = {
+  startIndex: number;
+  lastIndex: number;
+};
diff --git a/ts/util/graphemeAwareSlice.ts b/ts/util/graphemeAwareSlice.ts
deleted file mode 100644
index 04d5ae0b3..000000000
--- a/ts/util/graphemeAwareSlice.ts
+++ /dev/null
@@ -1,34 +0,0 @@
-// Copyright 2021-2022 Signal Messenger, LLC
-// SPDX-License-Identifier: AGPL-3.0-only
-
-export function graphemeAwareSlice(
-  str: string,
-  length: number,
-  buffer = 100
-): {
-  hasReadMore: boolean;
-  text: string;
-} {
-  if (str.length <= length + buffer) {
-    return { text: str, hasReadMore: false };
-  }
-
-  let text: string | undefined;
-
-  for (const { index } of new Intl.Segmenter().segment(str)) {
-    if (!text && index >= length) {
-      text = str.slice(0, index);
-    }
-    if (text && index > length) {
-      return {
-        text,
-        hasReadMore: true,
-      };
-    }
-  }
-
-  return {
-    text: str,
-    hasReadMore: false,
-  };
-}