diff --git a/src/pretix/base/email.py b/src/pretix/base/email.py
index e1efce0b03..395513286a 100644
--- a/src/pretix/base/email.py
+++ b/src/pretix/base/email.py
@@ -133,11 +133,11 @@ class TemplateBasedMailRenderer(BaseHTMLMailRenderer):
     def template_name(self):
         raise NotImplementedError()
 
-    def compile_markdown(self, plaintext):
-        return markdown_compile_email(plaintext)
+    def compile_markdown(self, plaintext, context=None):
+        return markdown_compile_email(plaintext, context=context)
 
     def render(self, plain_body: str, plain_signature: str, subject: str, order, position, context) -> str:
-        body_md = self.compile_markdown(plain_body)
+        body_md = self.compile_markdown(plain_body, context)
         if context:
             body_md = format_map(body_md, context=context, mode=SafeFormatter.MODE_RICH_TO_HTML)
         htmlctx = {
diff --git a/src/pretix/base/services/mail.py b/src/pretix/base/services/mail.py
index 03bd489e7e..3e05e9792a 100644
--- a/src/pretix/base/services/mail.py
+++ b/src/pretix/base/services/mail.py
@@ -222,7 +222,7 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
                     'invoice_company': ''
                 })
         renderer = ClassicMailRenderer(None, organizer)
-        content_plain = body_plain = render_mail(template, context)
+        body_plain = render_mail(template, context, placeholder_mode=SafeFormatter.MODE_RICH_TO_PLAIN)
         subject = str(subject).format_map(TolerantDict(context))
         sender = (
             sender or
@@ -316,6 +316,7 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
 
         with override(timezone):
             try:
+                content_plain = render_mail(template, context, placeholder_mode=None)
                 if plain_text_only:
                     body_html = None
                 elif 'context' in inspect.signature(renderer.render).parameters:
@@ -751,11 +752,11 @@ def mail_send(*args, **kwargs):
     mail_send_task.apply_async(args=args, kwargs=kwargs)
 
 
-def render_mail(template, context):
+def render_mail(template, context, placeholder_mode=SafeFormatter.MODE_RICH_TO_PLAIN):
     if isinstance(template, LazyI18nString):
         body = str(template)
-        if context:
-            body = format_map(body, context, mode=SafeFormatter.MODE_IGNORE_RICH)
+        if context and placeholder_mode:
+            body = format_map(body, context, mode=placeholder_mode)
     else:
         tpl = get_template(template)
         body = tpl.render(context)
diff --git a/src/pretix/base/services/placeholders.py b/src/pretix/base/services/placeholders.py
index c4cdc03c3f..9376748eb6 100644
--- a/src/pretix/base/services/placeholders.py
+++ b/src/pretix/base/services/placeholders.py
@@ -26,7 +26,7 @@ from decimal import Decimal
 
 from django.dispatch import receiver
 from django.utils.formats import date_format
-from django.utils.html import escape
+from django.utils.html import escape, mark_safe
 from django.utils.timezone import now
 from django.utils.translation import gettext_lazy as _
 
@@ -123,6 +123,10 @@ class BaseRichTextPlaceholder(BaseTextPlaceholder):
     def identifier(self):
         return self._identifier
 
+    @property
+    def allowed_in_plain_content(self):
+        return False
+
     @property
     def required_context(self):
         return self._args
@@ -194,6 +198,33 @@ class SimpleButtonPlaceholder(BaseRichTextPlaceholder):
         return f'{text}: {url}'
 
 
+class MarkdownTextPlaceholder(BaseRichTextPlaceholder):
+    def __init__(self, identifier, args, func, sample, inline):
+        super().__init__(identifier, args)
+        self._func = func
+        self._sample = sample
+        self._snippet = inline
+
+    @property
+    def allowed_in_plain_content(self):
+        return self._snippet
+
+    def render_plain(self, **context):
+        return self._func(**{k: context[k] for k in self._args})
+
+    def render_html(self, **context):
+        return mark_safe(markdown_compile_email(self.render_plain(**context), snippet=self._snippet))
+
+    def render_sample_plain(self, event):
+        if callable(self._sample):
+            return self._sample(event)
+        else:
+            return self._sample
+
+    def render_sample_html(self, event):
+        return mark_safe(markdown_compile_email(self.render_sample_plain(event), snippet=self._snippet))
+
+
 class PlaceholderContext(SafeFormatter):
     """
     Holds the contextual arguments and corresponding list of available placeholders for formatting
@@ -574,7 +605,7 @@ def base_placeholders(sender, **kwargs):
             'invoice_company', ['invoice_address'], lambda invoice_address: invoice_address.company or '',
             _('Sample Corporation')
         ),
-        SimpleFunctionalTextPlaceholder(
+        MarkdownTextPlaceholder(
             'orders', ['event', 'orders'], lambda event, orders: '\n' + '\n\n'.join(
                 '* {} - {}'.format(
                     order.full_code,
@@ -604,6 +635,7 @@ def base_placeholders(sender, **kwargs):
                     {'code': 'OPKSB', 'secret': '09pjdksflosk3njd', 'hash': 'stuvwxy2z'}
                 ]
             ),
+            inline=False,
         ),
         SimpleFunctionalTextPlaceholder(
             'hours', ['event', 'waiting_list_entry'], lambda event, waiting_list_entry:
@@ -618,12 +650,13 @@ def base_placeholders(sender, **kwargs):
             'code', ['waiting_list_voucher'], lambda waiting_list_voucher: waiting_list_voucher.code,
             '68CYU2H6ZTP3WLK5'
         ),
-        SimpleFunctionalTextPlaceholder(
+        MarkdownTextPlaceholder(
             # join vouchers with two spaces at end of line so markdown-parser inserts a <br>
             'voucher_list', ['voucher_list'], lambda voucher_list: '  \n'.join(voucher_list),
-            '    68CYU2H6ZTP3WLK5\n    7MB94KKPVEPSMVF2'
+            '68CYU2H6ZTP3WLK5  \n7MB94KKPVEPSMVF2',
+            inline=False,
         ),
-        SimpleFunctionalTextPlaceholder(
+        MarkdownTextPlaceholder(
             # join vouchers with two spaces at end of line so markdown-parser inserts a <br>
             'voucher_url_list', ['event', 'voucher_list'],
             lambda event, voucher_list: '  \n'.join([
@@ -638,6 +671,7 @@ def base_placeholders(sender, **kwargs):
                 ) + '?voucher=' + c
                 for c in ['68CYU2H6ZTP3WLK5', '7MB94KKPVEPSMVF2']
             ]),
+            inline=False,
         ),
         SimpleFunctionalTextPlaceholder(
             'url', ['event', 'voucher_list'], lambda event, voucher_list: build_absolute_uri(event, 'presale:event.index', kwargs={
@@ -656,13 +690,13 @@ def base_placeholders(sender, **kwargs):
             'comment', ['comment'], lambda comment: comment,
             _('An individual text with a reason can be inserted here.'),
         ),
-        SimpleFunctionalTextPlaceholder(
+        MarkdownTextPlaceholder(
             'payment_info', ['order', 'payments'], _placeholder_payments,
-            _('The amount has been charged to your card.'),
+            _('The amount has been charged to your card.'), inline=False,
         ),
-        SimpleFunctionalTextPlaceholder(
+        MarkdownTextPlaceholder(
             'payment_info', ['payment_info'], lambda payment_info: payment_info,
-            _('Please transfer money to this bank account: 9999-9999-9999-9999'),
+            _('Please transfer money to this bank account: 9999-9999-9999-9999'), inline=False,
         ),
         SimpleFunctionalTextPlaceholder(
             'attendee_name', ['position'], lambda position: position.attendee_name,
@@ -719,13 +753,13 @@ def base_placeholders(sender, **kwargs):
         ))
 
     for k, v in sender.meta_data.items():
-        ph.append(SimpleFunctionalTextPlaceholder(
+        ph.append(MarkdownTextPlaceholder(
             'meta_%s' % k, ['event'], lambda event, k=k: event.meta_data[k],
-            v
+            v, inline=True,
         ))
-        ph.append(SimpleFunctionalTextPlaceholder(
+        ph.append(MarkdownTextPlaceholder(
             'meta_%s' % k, ['event_or_subevent'], lambda event_or_subevent, k=k: event_or_subevent.meta_data[k],
-            v
+            v, inline=True,
         ))
 
     return ph
@@ -753,7 +787,7 @@ def get_available_placeholders(event, base_parameters, rich=False):
         if not isinstance(val, (list, tuple)):
             val = [val]
         for v in val:
-            if isinstance(v, BaseRichTextPlaceholder) and not rich:
+            if isinstance(v, BaseRichTextPlaceholder) and not rich and not v.allowed_in_plain_content:
                 continue
             if all(rp in base_parameters for rp in v.required_context):
                 params[v.identifier] = v
@@ -775,13 +809,13 @@ def get_sample_context(event, context_parameters, rich=True):
                 )
             )
         elif str(sample).strip().startswith('* ') or str(sample).startswith('  '):
-            context_dict[k] = '<div class="placeholder" title="{}">{}</div>'.format(
+            context_dict[k] = mark_safe('<div class="placeholder" title="{}">{}</div>'.format(
                 lbl,
                 markdown_compile_email(str(sample))
-            )
+            ))
         else:
-            context_dict[k] = '<span class="placeholder" title="{}">{}</span>'.format(
+            context_dict[k] = mark_safe('<span class="placeholder" title="{}">{}</span>'.format(
                 lbl,
                 escape(sample)
-            )
+            ))
     return context_dict
diff --git a/src/pretix/base/templatetags/rich_text.py b/src/pretix/base/templatetags/rich_text.py
index f38cdeab8c..954e093ffd 100644
--- a/src/pretix/base/templatetags/rich_text.py
+++ b/src/pretix/base/templatetags/rich_text.py
@@ -44,6 +44,7 @@ from django.conf import settings
 from django.core import signing
 from django.urls import reverse
 from django.utils.functional import SimpleLazyObject
+from django.utils.html import escape
 from django.utils.http import url_has_allowed_host_and_scheme
 from django.utils.safestring import mark_safe
 from markdown import Extension
@@ -52,6 +53,8 @@ from markdown.postprocessors import Postprocessor
 from markdown.treeprocessors import UnescapeTreeprocessor
 from tlds import tld_set
 
+from pretix.helpers.format import SafeFormatter, format_map
+
 register = template.Library()
 
 
@@ -321,27 +324,44 @@ class LinkifyAndCleanExtension(Extension):
         )
 
 
-def markdown_compile_email(source, allowed_tags=ALLOWED_TAGS, allowed_attributes=ALLOWED_ATTRIBUTES):
+def markdown_compile_email(source, allowed_tags=None, allowed_attributes=ALLOWED_ATTRIBUTES, snippet=False, context=None):
+    if allowed_tags is None:
+        allowed_tags = ALLOWED_TAGS_SNIPPET if snippet else ALLOWED_TAGS
+
+    context_callbacks = []
+    if context:
+        # This is a workaround to fix placeholders in URL targets
+        def context_callback(attrs, new=False):
+            if (None, "href") in attrs and "{" in attrs[None, "href"]:
+                # Do not use MODE_RICH_TO_HTML to avoid recursive linkification
+                attrs[None, "href"] = escape(format_map(attrs[None, "href"], context=context, mode=SafeFormatter.MODE_RICH_TO_PLAIN))
+            return attrs
+
+        context_callbacks.append(context_callback)
+
     linker = bleach.Linker(
         url_re=URL_RE,
         email_re=EMAIL_RE,
-        callbacks=DEFAULT_CALLBACKS + [truelink_callback, abslink_callback],
+        callbacks=context_callbacks + DEFAULT_CALLBACKS + [truelink_callback, abslink_callback],
         parse_email=True
     )
+    exts = [
+        'markdown.extensions.sane_lists',
+        'markdown.extensions.tables',
+        EmailNl2BrExtension(),
+        LinkifyAndCleanExtension(
+            linker,
+            tags=set(allowed_tags),
+            attributes=allowed_attributes,
+            protocols=ALLOWED_PROTOCOLS,
+            strip=snippet,
+        )
+    ]
+    if snippet:
+        exts.append(SnippetExtension())
     return markdown.markdown(
         source,
-        extensions=[
-            'markdown.extensions.sane_lists',
-            'markdown.extensions.tables',
-            EmailNl2BrExtension(),
-            LinkifyAndCleanExtension(
-                linker,
-                tags=set(allowed_tags),
-                attributes=allowed_attributes,
-                protocols=ALLOWED_PROTOCOLS,
-                strip=False,
-            )
-        ]
+        extensions=exts
     )
 
 
diff --git a/src/pretix/control/forms/vouchers.py b/src/pretix/control/forms/vouchers.py
index 5138b7b7cd..63f8d3069e 100644
--- a/src/pretix/control/forms/vouchers.py
+++ b/src/pretix/control/forms/vouchers.py
@@ -308,8 +308,8 @@ class VoucherBulkForm(VoucherForm):
     )
     Recipient = namedtuple('Recipient', 'email number name tag')
 
-    def _set_field_placeholders(self, fn, base_parameters):
-        placeholders = get_available_placeholders(self.instance.event, base_parameters)
+    def _set_field_placeholders(self, fn, base_parameters, rich=False):
+        placeholders = get_available_placeholders(self.instance.event, base_parameters, rich=rich)
         ht = format_placeholders_help_text(placeholders, self.instance.event)
 
         if self.fields[fn].help_text:
@@ -345,7 +345,7 @@ class VoucherBulkForm(VoucherForm):
     def __init__(self, *args, **kwargs):
         super().__init__(*args, **kwargs)
         self._set_field_placeholders('send_subject', ['event', 'name'])
-        self._set_field_placeholders('send_message', ['event', 'voucher_list', 'name'])
+        self._set_field_placeholders('send_message', ['event', 'voucher_list', 'name'], rich=True)
 
         with language(self.instance.event.settings.locale, self.instance.event.settings.region):
             for f in ("send_subject", "send_message"):
diff --git a/src/pretix/helpers/format.py b/src/pretix/helpers/format.py
index 33549ed8b2..ebbdba8eb9 100644
--- a/src/pretix/helpers/format.py
+++ b/src/pretix/helpers/format.py
@@ -22,6 +22,8 @@
 import logging
 from string import Formatter
 
+from django.utils.html import conditional_escape
+
 logger = logging.getLogger(__name__)
 
 
@@ -40,11 +42,10 @@ class SafeFormatter(Formatter):
     Customized version of ``str.format`` that (a) behaves just like ``str.format_map`` and
     (b) does not allow any unwanted shenanigans like attribute access or format specifiers.
     """
-    MODE_IGNORE_RICH = 0
     MODE_RICH_TO_PLAIN = 1
     MODE_RICH_TO_HTML = 2
 
-    def __init__(self, context, raise_on_missing=False, mode=MODE_IGNORE_RICH):
+    def __init__(self, context, raise_on_missing=False, mode=MODE_RICH_TO_PLAIN):
         self.context = context
         self.raise_on_missing = raise_on_missing
         self.mode = mode
@@ -55,22 +56,26 @@ class SafeFormatter(Formatter):
     def get_value(self, key, args, kwargs):
         if not self.raise_on_missing and key not in self.context:
             return '{' + str(key) + '}'
-        r = self.context[key]
-        if isinstance(r, PlainHtmlAlternativeString):
-            if self.mode == self.MODE_IGNORE_RICH:
-                return '{' + str(key) + '}'
-            elif self.mode == self.MODE_RICH_TO_PLAIN:
-                return r.plain
+        return self.context[key]
+
+    def _prepare_value(self, value):
+        if isinstance(value, PlainHtmlAlternativeString):
+            if self.mode == self.MODE_RICH_TO_PLAIN:
+                return value.plain
             elif self.mode == self.MODE_RICH_TO_HTML:
-                return r.html
-        return r
+                return value.html
+        else:
+            value = str(value)
+            if self.mode == self.MODE_RICH_TO_HTML:
+                value = conditional_escape(value)
+            return value
 
     def format_field(self, value, format_spec):
         # Ignore format_spec
-        return super().format_field(value, '')
+        return super().format_field(self._prepare_value(value), '')
 
 
-def format_map(template, context, raise_on_missing=False, mode=SafeFormatter.MODE_IGNORE_RICH):
+def format_map(template, context, raise_on_missing=False, mode=SafeFormatter.MODE_RICH_TO_PLAIN):
     if not isinstance(template, str):
         template = str(template)
     return SafeFormatter(context, raise_on_missing, mode=mode).format(template)
diff --git a/src/tests/base/test_mail.py b/src/tests/base/test_mail.py
index a9ca4f20e1..da276aa970 100644
--- a/src/tests/base/test_mail.py
+++ b/src/tests/base/test_mail.py
@@ -33,6 +33,8 @@
 # License for the specific language governing permissions and limitations under the License.
 
 import os
+import re
+from email.mime.text import MIMEText
 
 import pytest
 from django.conf import settings
@@ -40,7 +42,9 @@ from django.core import mail as djmail
 from django.utils.timezone import now
 from django.utils.translation import gettext_lazy as _
 from django_scopes import scope
+from i18nfield.strings import LazyI18nString
 
+from pretix.base.email import get_email_context
 from pretix.base.models import Event, Organizer, User
 from pretix.base.services.mail import mail
 
@@ -48,10 +52,14 @@ from pretix.base.services.mail import mail
 @pytest.fixture
 def env():
     o = Organizer.objects.create(name='Dummy', slug='dummy')
+    prop1 = o.meta_properties.get_or_create(name="Test")[0]
+    prop2 = o.meta_properties.get_or_create(name="Website")[0]
     event = Event.objects.create(
         organizer=o, name='Dummy', slug='dummy',
         date_from=now()
     )
+    event.meta_values.update_or_create(property=prop1, defaults={'value': "*Beep*"})
+    event.meta_values.update_or_create(property=prop2, defaults={'value': "https://example.com"})
     user = User.objects.create_user('dummy@dummy.dummy', 'dummy')
     user.email = 'dummy@dummy.dummy'
     user.save()
@@ -158,8 +166,95 @@ def test_send_mail_with_user_locale(env):
 def test_sendmail_placeholder(env):
     djmail.outbox = []
     event, user, organizer = env
-    mail('dummy@dummy.dummy', '{event} Test subject', 'mailtest.txt', {"event": event}, event)
+    mail('dummy@dummy.dummy', '{event} Test subject', 'mailtest.txt', {"event": event.name}, event)
 
     assert len(djmail.outbox) == 1
     assert djmail.outbox[0].to == [user.email]
     assert djmail.outbox[0].subject == 'Dummy Test subject'
+
+
+def _extract_html(mail):
+    for content, mimetype in mail.alternatives:
+        if "multipart/related" in mimetype:
+            for sp in content._payload:
+                if isinstance(sp, MIMEText):
+                    return sp._payload
+                    break
+        elif "text/html" in mimetype:
+            return content
+
+
+@pytest.mark.django_db
+def test_placeholder_html_rendering_from_template(env):
+    djmail.outbox = []
+    event, user, organizer = env
+    event.name = "<strong>event & co. kg</strong>"
+    event.save()
+    mail('dummy@dummy.dummy', '{event} Test subject', 'mailtest.txt', get_email_context(
+        event=event,
+        payment_info="**IBAN**: 123  \n**BIC**: 456",
+    ), event)
+
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == [user.email]
+    assert 'Event name: <strong>event & co. kg</strong>' in djmail.outbox[0].body
+    assert '**IBAN**: 123  \n**BIC**: 456' in djmail.outbox[0].body
+    assert '**Meta**: *Beep*' in djmail.outbox[0].body
+    assert 'Event website: [<strong>event & co. kg</strong>](https://example.org/dummy)' in djmail.outbox[0].body
+    assert 'Other website: [<strong>event & co. kg</strong>](https://example.com)' in djmail.outbox[0].body
+    assert '&lt;' not in djmail.outbox[0].body
+    assert '&amp;' not in djmail.outbox[0].body
+    html = _extract_html(djmail.outbox[0])
+
+    assert '<strong>event' not in html
+    assert 'Event name: &lt;strong&gt;event &amp; co. kg&lt;/strong&gt;' in html
+    assert '<strong>IBAN</strong>: 123<br/>\n<strong>BIC</strong>: 456' in html
+    assert '<strong>Meta</strong>: <em>Beep</em>' in html
+    assert re.search(
+        r'Event website: <a href="https://example.org/dummy" rel="noopener" style="[^"]+" target="_blank">&lt;strong&gt;event &amp; co. kg&lt;/strong&gt;</a>',
+        html
+    )
+    assert re.search(
+        r'Other website: <a href="https://example.com" rel="noopener" style="[^"]+" target="_blank">&lt;strong&gt;event &amp; co. kg&lt;/strong&gt;</a>',
+        html
+    )
+
+
+@pytest.mark.django_db
+def test_placeholder_html_rendering_from_string(env):
+    template = LazyI18nString({
+        "en": "Event name: {event}\n\nPayment info:\n{payment_info}\n\n**Meta**: {meta_Test}\n\n"
+              "Event website: [{event}](https://example.org/{event_slug})\n\n"
+              "Other website: [{event}]({meta_Website})"
+    })
+    djmail.outbox = []
+    event, user, organizer = env
+    event.name = "<strong>event & co. kg</strong>"
+    event.save()
+    mail('dummy@dummy.dummy', '{event} Test subject', template, get_email_context(
+        event=event,
+        payment_info="**IBAN**: 123  \n**BIC**: 456",
+    ), event)
+
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == [user.email]
+    assert 'Event name: <strong>event & co. kg</strong>' in djmail.outbox[0].body
+    assert 'Event website: [<strong>event & co. kg</strong>](https://example.org/dummy)' in djmail.outbox[0].body
+    assert 'Other website: [<strong>event & co. kg</strong>](https://example.com)' in djmail.outbox[0].body
+    assert '**IBAN**: 123  \n**BIC**: 456' in djmail.outbox[0].body
+    assert '**Meta**: *Beep*' in djmail.outbox[0].body
+    assert '&lt;' not in djmail.outbox[0].body
+    assert '&amp;' not in djmail.outbox[0].body
+    html = _extract_html(djmail.outbox[0])
+    assert '<strong>event' not in html
+    assert 'Event name: &lt;strong&gt;event &amp; co. kg&lt;/strong&gt;' in html
+    assert '<strong>IBAN</strong>: 123<br/>\n<strong>BIC</strong>: 456' in html
+    assert '<strong>Meta</strong>: <em>Beep</em>' in html
+    assert re.search(
+        r'Event website: <a href="https://example.org/dummy" rel="noopener" style="[^"]+" target="_blank">&lt;strong&gt;event &amp; co. kg&lt;/strong&gt;</a>',
+        html
+    )
+    assert re.search(
+        r'Other website: <a href="https://example.com" rel="noopener" style="[^"]+" target="_blank">&lt;strong&gt;event &amp; co. kg&lt;/strong&gt;</a>',
+        html
+    )
diff --git a/src/tests/helpers/test_format.py b/src/tests/helpers/test_format.py
index 5ab5c2569b..5ed3ac9b15 100644
--- a/src/tests/helpers/test_format.py
+++ b/src/tests/helpers/test_format.py
@@ -40,6 +40,5 @@ def test_format_alternatives():
         )
     }
 
-    assert format_map("Foo {bar}", ctx, mode=SafeFormatter.MODE_IGNORE_RICH) == "Foo {bar}"
     assert format_map("Foo {bar}", ctx, mode=SafeFormatter.MODE_RICH_TO_PLAIN) == "Foo plain text"
     assert format_map("Foo {bar}", ctx, mode=SafeFormatter.MODE_RICH_TO_HTML) == "Foo <span>HTML version</span>"
diff --git a/src/tests/templates/mailtest.txt b/src/tests/templates/mailtest.txt
index 71139e00cb..1bc1487d31 100644
--- a/src/tests/templates/mailtest.txt
+++ b/src/tests/templates/mailtest.txt
@@ -1,4 +1,13 @@
 {% load i18n %}
 This is a test file for sending mails.
+Event name: {event}
 {% get_current_language as LANGUAGE_CODE %}
 The language code used for rendering this email is {{ LANGUAGE_CODE }}.
+
+Payment info:
+{payment_info}
+
+**Meta**: {meta_Test}
+
+Event website: [{event}](https://example.org/{event_slug})
+Other website: [{event}]({meta_Website})
\ No newline at end of file