diff --git a/src/client/accounts/add-edit-page.vala b/src/client/accounts/add-edit-page.vala
index 62e19566..66a05a95 100644
--- a/src/client/accounts/add-edit-page.vala
+++ b/src/client/accounts/add-edit-page.vala
@@ -603,7 +603,7 @@ public class AddEditPage : Gtk.Box {
     
     private void on_signature_stack_changed() {
         if (signature_stack.visible_child_name == "preview_window")
-            preview_webview.load_html(Geary.HTML.smart_escape(email_signature, true), null);
+            preview_webview.load_html(Geary.HTML.smart_escape(email_signature), null);
     }
 
     private uint16 get_default_smtp_port() {
diff --git a/src/client/composer/composer-widget.vala b/src/client/composer/composer-widget.vala
index a88e5588..978cdd08 100644
--- a/src/client/composer/composer-widget.vala
+++ b/src/client/composer/composer-widget.vala
@@ -2150,7 +2150,7 @@ public class ComposerWidget : Gtk.EventBox {
             }
 
             account_sig = (!Geary.String.is_empty_or_whitespace(account_sig))
-                ? Geary.HTML.smart_escape(account_sig, true)
+                ? Geary.HTML.smart_escape(account_sig)
                 : "";
         }
 
diff --git a/src/engine/rfc822/rfc822-utils.vala b/src/engine/rfc822/rfc822-utils.vala
index 44acbc49..7087cb7f 100644
--- a/src/engine/rfc822/rfc822-utils.vala
+++ b/src/engine/rfc822/rfc822-utils.vala
@@ -302,12 +302,14 @@ public string quote_email_for_forward(Geary.Email email, string? quote, TextForm
     return quoted;
 }
 
-private string quote_body(Geary.Email email, string? quote, bool use_quotes, TextFormat format)
+private string quote_body(Geary.Email email,
+                          string? html_quote,
+                          bool use_quotes,
+                          TextFormat format)
     throws Error {
     Message? message = email.get_message();
-    bool preserve_whitespace = !message.has_html_body();
     string? body_text = null;
-    if (quote == null) {
+    if (String.is_empty(html_quote)) {
         switch (format) {
         case TextFormat.HTML:
             body_text = message.has_html_body()
@@ -322,7 +324,7 @@ private string quote_body(Geary.Email email, string? quote, bool use_quotes, Tex
             break;
         }
     } else {
-        body_text = Geary.HTML.smart_escape(quote, preserve_whitespace);
+        body_text = html_quote;
     }
 
     // Wrap the whole thing in a blockquote.
diff --git a/src/engine/util/util-html.vala b/src/engine/util/util-html.vala
index 522c1192..ce76b1d7 100644
--- a/src/engine/util/util-html.vala
+++ b/src/engine/util/util-html.vala
@@ -10,6 +10,8 @@ namespace Geary.HTML {
 // Originally from here: http://daringfireball.net/2010/07/improved_regex_for_matching_urls
 public const string URL_REGEX = "(?i)\\b((?:[a-z][\\w-]+:(?:/{1,3}|[a-z0-9%])|www\\d{0,3}[.]|[a-z0-9.\\-]+[.][a-z]{2,4}/)(?:[^\\s()<>]+|\\(([^\\s()<>]+|(\\([^\\s()<>]+\\)))*\\))+(?:\\(([^\\s()<>]+|(\\([^\\s()<>]+\\)))*\\)|[^\\s`!()\\[\\]{};:'\".,<>?«»“”‘’]))";
 
+private Regex WHITESPACE_REGEX;
+
 private int init_count = 0;
 private Gee.HashSet<string>? breaking_elements;
 private Gee.HashSet<string>? spacing_elements;
@@ -27,6 +29,12 @@ public void init() {
         return;
 
     init_element_sets();
+
+    try {
+        WHITESPACE_REGEX = new Regex("(\\R|\\t|[ ]+)");
+    } catch (GLib.Error err) {
+        assert(true);
+    }
 }
 
 private void init_element_sets() {
@@ -95,20 +103,58 @@ private void init_element_sets() {
     });
 }
 
+/** Converts plain text to HTML with reserved characters escaped. */
 public inline string escape_markup(string? plain) {
-    return (!String.is_empty(plain) && plain.validate()) ? Markup.escape_text(plain) : "";
+    return (!String.is_empty(plain) && plain.validate())
+        ? Markup.escape_text(plain) : "";
 }
 
+/** Converts plain text to HTML with whitespace (SP, CR, LF) preserved. */
 public string preserve_whitespace(string? text) {
-    if (String.is_empty(text))
-        return "";
-    
-    string output = text.replace(" ", "&nbsp;");
-    output = output.replace("\r\n", "<br />");
-    output = output.replace("\n", "<br />");
-    output = output.replace("\r", "<br />");
+    string preserved = "";
+    if (!String.is_empty(text)) {
+        try {
+            preserved = WHITESPACE_REGEX.replace_eval(
+                text, -1, 0, 0, (info, result) => {
+                    string match = info.fetch(0);
+                    if (match[0] == ' ') {
+                        result.append_c(' ');
+                        for (int len = match.length - 1; len > 0; len--) {
+                            result.append("&nbsp;");
+                    }
+                    } else if (match == "\t") {
+                        result.append(" &nbsp;&nbsp;&nbsp;");
+                    } else {
+                        result.append("<br>");
+                    }
+                    return false;
+                });
+        } catch (Error err) {
+            debug("Error preserving whitespace: %s", err.message);
+        }
+    }
+    return preserved;
+}
 
-    return output;
+/**
+ * Escape reserved HTML entities and preserves whitespace, if needed.
+ *
+ * Returns a string with reserved HTML entities escaped and
+ * whitespace preserved if the given string does not have HTML
+ * tags.
+ */
+public string smart_escape(string? text) {
+    string escaped = text ?? "";
+    if (text != null) {
+        bool is_html = Regex.match_simple(
+            "<[A-Z]+ ?(?: [^>]*)?\\/?>", text, RegexCompileFlags.CASELESS
+        );
+        if (!is_html) {
+            escaped = escape_markup(escaped);
+            escaped = preserve_whitespace(escaped);
+        }
+    }
+    return escaped;
 }
 
 /**
@@ -168,22 +214,4 @@ private void recurse_html_nodes_for_text(Xml.Node? node,
     }
 }
 
-// Escape reserved HTML entities if the string does not have HTML
-// tags.  If there are no tags, or if preserve_whitespace_in_html is
-// true, wrap the string a div to preserve whitespace.
-public string smart_escape(string? text, bool preserve_whitespace_in_html) {
-    if (text == null)
-        return text;
-
-    string res = text;
-    if (!Regex.match_simple("<[A-Z]*(?: [^>]*)?\\/?>", res,
-                            RegexCompileFlags.CASELESS)) {
-        res = Geary.HTML.escape_markup(res);
-        preserve_whitespace_in_html = true;
-    }
-    if (preserve_whitespace_in_html)
-        res = @"<div style='white-space: pre-wrap;'>$res</div>";
-    return res;
-}
-
 }
diff --git a/test/engine/util-html-test.vala b/test/engine/util-html-test.vala
index 4f3b112f..b59230de 100644
--- a/test/engine/util-html-test.vala
+++ b/test/engine/util-html-test.vala
@@ -9,6 +9,7 @@ class Geary.HTML.UtilTest : TestCase {
 
     public UtilTest() {
         base("Geary.HTML.Util");
+        add_test("preserve_whitespace", preserve_whitespace);
         add_test("smart_escape_div", smart_escape_div);
         add_test("smart_escape_no_closing_tag", smart_escape_no_closing_tag);
         add_test("smart_escape_img", smart_escape_img);
@@ -19,39 +20,62 @@ class Geary.HTML.UtilTest : TestCase {
         add_test("remove_html_tags", remove_html_tags);
     }
 
+    public void preserve_whitespace() throws GLib.Error {
+        assert_string("some text", Geary.HTML.smart_escape("some text"));
+        assert_string("some &nbsp;text", Geary.HTML.smart_escape("some  text"));
+        assert_string("some &nbsp;&nbsp;text", Geary.HTML.smart_escape("some   text"));
+        assert_string("some &nbsp;&nbsp;&nbsp;text", Geary.HTML.smart_escape("some\ttext"));
+
+        assert_string("some<br>text", Geary.HTML.smart_escape("some\ntext"));
+        assert_string("some<br>text", Geary.HTML.smart_escape("some\rtext"));
+        assert_string("some<br>text", Geary.HTML.smart_escape("some\r\ntext"));
+
+        assert_string("some<br><br>text", Geary.HTML.smart_escape("some\n\ntext"));
+        assert_string("some<br><br>text", Geary.HTML.smart_escape("some\r\rtext"));
+        assert_string("some<br><br>text", Geary.HTML.smart_escape("some\n\rtext"));
+        assert_string("some<br><br>text", Geary.HTML.smart_escape("some\r\n\r\ntext"));
+    }
+
     public void smart_escape_div() throws Error {
         string html = "<div>ohhai</div>";
-        assert(Geary.HTML.smart_escape(html, false) == html);
+        assert(Geary.HTML.smart_escape(html) == html);
     }
 
     public void smart_escape_no_closing_tag() throws Error {
         string html = "<div>ohhai";
-        assert(Geary.HTML.smart_escape(html, false) == html);
+        assert(Geary.HTML.smart_escape(html) == html);
     }
 
     public void smart_escape_img() throws Error {
         string html = "<img src=\"http://example.com/lol.gif\">";
-        assert(Geary.HTML.smart_escape(html, false) == html);
+        assert(Geary.HTML.smart_escape(html) == html);
     }
 
     public void smart_escape_xhtml_img() throws Error {
         string html = "<img src=\"http://example.com/lol.gif\"/>";
-        assert(Geary.HTML.smart_escape(html, false) == html);
+        assert(Geary.HTML.smart_escape(html) == html);
     }
 
     public void smart_escape_mixed() throws Error {
         string html = "mixed <div>ohhai</div> text";
-        assert(Geary.HTML.smart_escape(html, false) == html);
+        assert(Geary.HTML.smart_escape(html) == html);
     }
 
-    public void smart_escape_text() throws Error {
-        string text = "some text";
-        assert(Geary.HTML.smart_escape(text, false) == "<div style='white-space: pre-wrap;'>some text</div>");
+    public void smart_escape_text() throws GLib.Error {
+        assert_string("some text", Geary.HTML.smart_escape("some text"));
+        assert_string("&lt;some text", Geary.HTML.smart_escape("<some text"));
+        assert_string("some text&gt;", Geary.HTML.smart_escape("some text>"));
     }
 
-    public void smart_escape_text_url() throws Error {
-        string text = "<http://example.com>";
-        assert(Geary.HTML.smart_escape(text, false) == "<div style='white-space: pre-wrap;'>&lt;http://example.com&gt;</div>");
+    public void smart_escape_text_url() throws GLib.Error {
+        assert_string(
+            "&lt;http://example.com&gt;",
+            Geary.HTML.smart_escape("<http://example.com>")
+        );
+        assert_string(
+            "&lt;http://example.com&gt;",
+            Geary.HTML.smart_escape("<http://example.com>")
+        );
     }
 
     public void remove_html_tags() throws Error {