diff --git a/internal/linkcheck/linkcheck_test.go b/internal/linkcheck/linkcheck_test.go
index bf27a8f..563c98b 100644
--- a/internal/linkcheck/linkcheck_test.go
+++ b/internal/linkcheck/linkcheck_test.go
@@ -31,7 +31,14 @@ var (
 	</html>`
 
 	expectedHTMLLinks = []string{
-		"http://example.com", "https://example.com", "HTTPS://EXAMPLE.COM", "http://localhost", "https://localhost", "https://127.0.0.1", "http://link with spaces", "http://example.com/?blaah=yes&test=true",
+		"http://example.com",
+		"https://example.com",
+		"HTTPS://EXAMPLE.COM",
+		"http://localhost",
+		"https://localhost",
+		"https://127.0.0.1",
+		"http://link with spaces",
+		"http://example.com/?blaah=yes&test=true",
 		"http://remote-host/style.css",  // css
 		"https://example.com/image.jpg", // images
 	}
@@ -41,10 +48,18 @@ var (
 		[http://localhost]
 		www.google.com < ignored
 		|||http://example.com/?some=query-string|||
+		// RFC2396 appendix E states angle brackets are recommended for text/plain emails to
+		// recognize potential spaces in between the URL
+		<https://example.com/ link with spaces>
 	`
 
 	expectedTextLinks = []string{
-		"http://example.com", "https://example.com", "HTTPS://EXAMPLE.COM", "http://localhost", "http://example.com/?some=query-string",
+		"http://example.com",
+		"https://example.com",
+		"HTTPS://EXAMPLE.COM",
+		"http://localhost",
+		"http://example.com/?some=query-string",
+		"https://example.com/ link with spaces",
 	}
 )
 
diff --git a/internal/linkcheck/main.go b/internal/linkcheck/main.go
index eaba8ba..f1c0db3 100644
--- a/internal/linkcheck/main.go
+++ b/internal/linkcheck/main.go
@@ -30,9 +30,28 @@ func RunTests(msg *storage.Message, followRedirects bool) (Response, error) {
 }
 
 func extractTextLinks(msg *storage.Message) []string {
+	testLinkRe := regexp.MustCompile(`(?im)([^<]\b)((http|https):\/\/([\-\w@:%_\+'!.~#?,&\/\/=;]+))`)
+	// RFC2396 appendix E states angle brackets are recommended for text/plain emails to
+	// recognize potential spaces in between the URL
+	// @see https://www.rfc-editor.org/rfc/rfc2396#appendix-E
+	bracketLinkRe := regexp.MustCompile(`(?im)<((http|https):\/\/([\-\w@:%_\+'!.~#?,&\/\/=;][^>]+))>`)
+
 	links := []string{}
 
-	links = append(links, linkRe.FindAllString(msg.Text, -1)...)
+	matches := testLinkRe.FindAllStringSubmatch(msg.Text, -1)
+	for _, match := range matches {
+		if len(match) > 0 {
+			links = append(links, match[2])
+		}
+	}
+
+	angleMatches := bracketLinkRe.FindAllStringSubmatch(msg.Text, -1)
+	for _, match := range angleMatches {
+		if len(match) > 0 {
+			link := strings.ReplaceAll(match[1], "\n", "")
+			links = append(links, link)
+		}
+	}
 
 	return links
 }
diff --git a/server/ui-src/components/message/MessageItem.vue b/server/ui-src/components/message/MessageItem.vue
index 643b19e..1369f26 100644
--- a/server/ui-src/components/message/MessageItem.vue
+++ b/server/ui-src/components/message/MessageItem.vue
@@ -290,15 +290,24 @@ export default {
 		textToHTML(s) {
 			let html = s;
 
-			// full links with http(s)
-			const re = /(\b(https?|ftp):\/\/[-\w@:%_+'!.~#?,&//=;]+)/gim;
-			html = html.replace(re, "˱˱˱a href=ˠˠˠ$&ˠˠˠ target=_blank rel=noopener˲˲˲$&˱˱˱/a˲˲˲");
+			// RFC2396 appendix E states angle brackets are recommended for text/plain emails to
+			// recognize potential spaces in between the URL
+			// @see https://www.rfc-editor.org/rfc/rfc2396#appendix-E
+			const angleLinks = /<((https?|ftp):\/\/[-\w@:%_+'!.~#?,&//=; ][^>]+)>/gim;
+			html = html.replace(angleLinks, "<˱˱˱a href=ˠˠˠ$1ˠˠˠ target=_blank rel=noopener˲˲˲$1˱˱˱/a˲˲˲>");
+
+			// find links without angle brackets, starting with http(s) or ftp
+			const regularLinks = /([^ˠ˲]\b)(((https?|ftp):\/\/[-\w@:%_+'!.~#?,&//=;]+))/gim;
+			html = html.replace(regularLinks, "$1˱˱˱a href=ˠˠˠ$2ˠˠˠ target=_blank rel=noopener˲˲˲$2˱˱˱/a˲˲˲");
 
 			// plain www links without https?:// prefix
-			const re2 = /(^|[^/])(www\.[\S]+(\b|$))/gim;
-			html = html.replace(re2, "$1˱˱˱a href=ˠˠˠhttp://$2ˠˠˠ target=ˠˠˠ_blankˠˠˠ rel=ˠˠˠnoopenerˠˠˠ˲˲˲$2˱˱˱/a˲˲˲");
+			const shortLinks = /(^|[^/])(www\.[\S]+(\b|$))/gim;
+			html = html.replace(
+				shortLinks,
+				"$1˱˱˱a href=ˠˠˠhttp://$2ˠˠˠ target=ˠˠˠ_blankˠˠˠ rel=ˠˠˠnoopenerˠˠˠ˲˲˲$2˱˱˱/a˲˲˲",
+			);
 
-			// escape to HTML & convert <>" back
+			// escape to HTML & convert <>" characters back
 			html = html
 				.replace(/&/g, "&amp;")
 				.replace(/</g, "&lt;")