diff --git a/Cargo.lock b/Cargo.lock
index 16a2bcd94..eb6a7a1e8 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -92,10 +92,10 @@ version = "4.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "17e913097e1a2124b46746c980134e8c954bc17a6a59bb3fde96f088d126dde6"
 dependencies = [
- "cssparser",
- "html5ever",
+ "cssparser 0.35.0",
+ "html5ever 0.35.0",
  "maplit",
- "tendril",
+ "tendril 0.4.3",
  "url",
 ]
 
@@ -801,7 +801,7 @@ checksum = "93698b29de5e97ad0ae26447b344c482a7284c737d9ddc5f9e52b74a336671bb"
 dependencies = [
  "chrono",
  "chrono-tz-build",
- "phf",
+ "phf 0.11.3",
 ]
 
 [[package]]
@@ -811,8 +811,8 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0c088aee841df9c3041febbb73934cfc39708749bf96dc827e3359cd39ef11b1"
 dependencies = [
  "parse-zoneinfo",
- "phf",
- "phf_codegen",
+ "phf 0.11.3",
+ "phf_codegen 0.11.3",
 ]
 
 [[package]]
@@ -1116,6 +1116,25 @@ dependencies = [
  "typenum",
 ]
 
+[[package]]
+name = "css-inline"
+version = "0.20.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "94c78ae84c4ea75d3734db18f768c7ce7ef5615fbd13987245db26c4a121771d"
+dependencies = [
+ "cssparser 0.36.0",
+ "html5ever 0.39.0",
+ "lru",
+ "memchr",
+ "precomputed-hash",
+ "rayon",
+ "reqwest",
+ "rustc-hash",
+ "selectors",
+ "smallvec",
+ "url",
+]
+
 [[package]]
 name = "cssparser"
 version = "0.35.0"
@@ -1125,7 +1144,20 @@ dependencies = [
  "cssparser-macros",
  "dtoa-short",
  "itoa",
- "phf",
+ "phf 0.11.3",
+ "smallvec",
+]
+
+[[package]]
+name = "cssparser"
+version = "0.36.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "dae61cf9c0abb83bd659dab65b7e4e38d8236824c85f0f804f173567bda257d2"
+dependencies = [
+ "cssparser-macros",
+ "dtoa-short",
+ "itoa",
+ "phf 0.13.1",
  "smallvec",
 ]
 
@@ -1528,6 +1560,7 @@ version = "0.0.0"
 dependencies = [
  "chrono",
  "claims",
+ "css-inline",
  "defguard_common",
  "humantime",
  "image",
@@ -2239,6 +2272,12 @@ version = "0.1.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "d9c4f5dac5e15c24eb999c26181a6ca40b39fe946cbe4c263c7209467bc83af2"
 
+[[package]]
+name = "foldhash"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "77ce24cb58228fbb8aa041425bb1050850ac19177686ea6e0f41a70416f56fdb"
+
 [[package]]
 name = "foreign-types"
 version = "0.3.2"
@@ -2582,7 +2621,18 @@ checksum = "9229cfe53dfd69f0609a49f65461bd93001ea1ef889cd5529dd176593f5338a1"
 dependencies = [
  "allocator-api2",
  "equivalent",
- "foldhash",
+ "foldhash 0.1.5",
+]
+
+[[package]]
+name = "hashbrown"
+version = "0.16.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "841d1cc9bed7f9236f321df977030373f4a4163ae1a7dbfe1a51a2c1a51d9100"
+dependencies = [
+ "allocator-api2",
+ "equivalent",
+ "foldhash 0.2.0",
 ]
 
 [[package]]
@@ -2670,10 +2720,20 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "55d958c2f74b664487a2035fe1dadb032c48718a03b63f3ab0b8537db8549ed4"
 dependencies = [
  "log",
- "markup5ever",
+ "markup5ever 0.35.0",
  "match_token",
 ]
 
+[[package]]
+name = "html5ever"
+version = "0.39.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "46a1761807faccc9a19e86944bbf40610014066306f96edcdedc2fb714bcb7b8"
+dependencies = [
+ "log",
+ "markup5ever 0.39.0",
+]
+
 [[package]]
 name = "htmlparser"
 version = "0.2.1"
@@ -3417,6 +3477,15 @@ dependencies = [
  "imgref",
 ]
 
+[[package]]
+name = "lru"
+version = "0.16.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7f66e8d5d03f609abc3a39e6f08e4164ebf1447a732906d39eb9b99b7919ef39"
+dependencies = [
+ "hashbrown 0.16.1",
+]
+
 [[package]]
 name = "lru-slab"
 version = "0.1.2"
@@ -3442,8 +3511,19 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "311fe69c934650f8f19652b3946075f0fc41ad8757dbb68f1ca14e7900ecc1c3"
 dependencies = [
  "log",
- "tendril",
- "web_atoms",
+ "tendril 0.4.3",
+ "web_atoms 0.1.3",
+]
+
+[[package]]
+name = "markup5ever"
+version = "0.39.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7122d987ec5f704ee56f6e5b41a7d93722e9aae27ae07cafa4036c4d3f9757de"
+dependencies = [
+ "log",
+ "tendril 0.5.0",
+ "web_atoms 0.2.3",
 ]
 
 [[package]]
@@ -4397,8 +4477,19 @@ version = "0.11.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1fd6780a80ae0c52cc120a26a1a42c1ae51b247a253e4e06113d23d2c2edd078"
 dependencies = [
- "phf_macros",
- "phf_shared",
+ "phf_macros 0.11.3",
+ "phf_shared 0.11.3",
+]
+
+[[package]]
+name = "phf"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c1562dc717473dbaa4c1f85a36410e03c047b2e7df7f45ee938fbef64ae7fadf"
+dependencies = [
+ "phf_macros 0.13.1",
+ "phf_shared 0.13.1",
+ "serde",
 ]
 
 [[package]]
@@ -4407,8 +4498,18 @@ version = "0.11.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "aef8048c789fa5e851558d709946d6d79a8ff88c0440c587967f8e94bfb1216a"
 dependencies = [
- "phf_generator",
- "phf_shared",
+ "phf_generator 0.11.3",
+ "phf_shared 0.11.3",
+]
+
+[[package]]
+name = "phf_codegen"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "49aa7f9d80421bca176ca8dbfebe668cc7a2684708594ec9f3c0db0805d5d6e1"
+dependencies = [
+ "phf_generator 0.13.1",
+ "phf_shared 0.13.1",
 ]
 
 [[package]]
@@ -4417,18 +4518,41 @@ version = "0.11.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3c80231409c20246a13fddb31776fb942c38553c51e871f8cbd687a4cfb5843d"
 dependencies = [
- "phf_shared",
+ "phf_shared 0.11.3",
  "rand 0.8.6",
 ]
 
+[[package]]
+name = "phf_generator"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "135ace3a761e564ec88c03a77317a7c6b80bb7f7135ef2544dbe054243b89737"
+dependencies = [
+ "fastrand",
+ "phf_shared 0.13.1",
+]
+
 [[package]]
 name = "phf_macros"
 version = "0.11.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f84ac04429c13a7ff43785d75ad27569f2951ce0ffd30a3321230db2fc727216"
 dependencies = [
- "phf_generator",
- "phf_shared",
+ "phf_generator 0.11.3",
+ "phf_shared 0.11.3",
+ "proc-macro2",
+ "quote",
+ "syn",
+]
+
+[[package]]
+name = "phf_macros"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "812f032b54b1e759ccd5f8b6677695d5268c588701effba24601f6932f8269ef"
+dependencies = [
+ "phf_generator 0.13.1",
+ "phf_shared 0.13.1",
  "proc-macro2",
  "quote",
  "syn",
@@ -4443,6 +4567,15 @@ dependencies = [
  "siphasher",
 ]
 
+[[package]]
+name = "phf_shared"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e57fef6bc5981e38c2ce2d63bfa546861309f875b8a75f092d1d54ae2d64f266"
+dependencies = [
+ "siphasher",
+]
+
 [[package]]
 name = "pin-project"
 version = "1.1.11"
@@ -5055,6 +5188,7 @@ dependencies = [
  "cookie",
  "cookie_store",
  "encoding_rs",
+ "futures-channel",
  "futures-core",
  "futures-util",
  "h2",
@@ -5394,6 +5528,25 @@ dependencies = [
  "libc",
 ]
 
+[[package]]
+name = "selectors"
+version = "0.36.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c5d9c0c92a92d33f08817311cf3f2c29a3538a8240e94a6a3c622ce652d7e00c"
+dependencies = [
+ "bitflags 2.11.1",
+ "cssparser 0.36.0",
+ "derive_more 2.1.1",
+ "log",
+ "new_debug_unreachable",
+ "phf 0.13.1",
+ "phf_codegen 0.13.1",
+ "precomputed-hash",
+ "rustc-hash",
+ "servo_arc",
+ "smallvec",
+]
+
 [[package]]
 name = "semver"
 version = "1.0.28"
@@ -5598,6 +5751,15 @@ dependencies = [
  "serde",
 ]
 
+[[package]]
+name = "servo_arc"
+version = "0.4.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "170fb83ab34de17dc69aa7c67482b22218ddb85da56546f9bd6b929e32a05930"
+dependencies = [
+ "stable_deref_trait",
+]
+
 [[package]]
 name = "sha-1"
 version = "0.10.1"
@@ -6062,19 +6224,43 @@ checksum = "bf776ba3fa74f83bf4b63c3dcbbf82173db2632ed8452cb2d891d33f459de70f"
 dependencies = [
  "new_debug_unreachable",
  "parking_lot",
- "phf_shared",
+ "phf_shared 0.11.3",
  "precomputed-hash",
  "serde",
 ]
 
+[[package]]
+name = "string_cache"
+version = "0.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a18596f8c785a729f2819c0f6a7eae6ebeebdfffbfe4214ae6b087f690e31901"
+dependencies = [
+ "new_debug_unreachable",
+ "parking_lot",
+ "phf_shared 0.13.1",
+ "precomputed-hash",
+]
+
 [[package]]
 name = "string_cache_codegen"
 version = "0.5.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "c711928715f1fe0fe509c53b43e993a9a557babc2d0a3567d0a3006f1ac931a0"
 dependencies = [
- "phf_generator",
- "phf_shared",
+ "phf_generator 0.11.3",
+ "phf_shared 0.11.3",
+ "proc-macro2",
+ "quote",
+]
+
+[[package]]
+name = "string_cache_codegen"
+version = "0.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "585635e46db231059f76c5849798146164652513eb9e8ab2685939dd90f29b69"
+dependencies = [
+ "phf_generator 0.13.1",
+ "phf_shared 0.13.1",
  "proc-macro2",
  "quote",
 ]
@@ -6225,6 +6411,16 @@ dependencies = [
  "utf-8",
 ]
 
+[[package]]
+name = "tendril"
+version = "0.5.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c4790fc369d5a530f4b544b094e31388b9b3a37c0f4652ade4505945f5660d24"
+dependencies = [
+ "new_debug_unreachable",
+ "utf-8",
+]
+
 [[package]]
 name = "tera"
 version = "1.20.1"
@@ -7159,10 +7355,22 @@ version = "0.1.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "57ffde1dc01240bdf9992e3205668b235e59421fd085e8a317ed98da0178d414"
 dependencies = [
- "phf",
- "phf_codegen",
- "string_cache",
- "string_cache_codegen",
+ "phf 0.11.3",
+ "phf_codegen 0.11.3",
+ "string_cache 0.8.9",
+ "string_cache_codegen 0.5.4",
+]
+
+[[package]]
+name = "web_atoms"
+version = "0.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "57a9779e9f04d2ac1ce317aee707aa2f6b773afba7b931222bff6983843b1576"
+dependencies = [
+ "phf 0.13.1",
+ "phf_codegen 0.13.1",
+ "string_cache 0.9.0",
+ "string_cache_codegen 0.6.1",
 ]
 
 [[package]]
diff --git a/crates/defguard_mail/Cargo.toml b/crates/defguard_mail/Cargo.toml
index 9ada5ddf2..c2219ac69 100644
--- a/crates/defguard_mail/Cargo.toml
+++ b/crates/defguard_mail/Cargo.toml
@@ -26,6 +26,7 @@ humantime.workspace = true
 image = "0.25" # match with qrforge
 mrml = "5.1"
 qrforge = {version = "0.1", default-features = false, features = ["image"]}
+css-inline = "0.20.2"
 
 [dev-dependencies]
 claims.workspace = true
diff --git a/crates/defguard_mail/src/templates.rs b/crates/defguard_mail/src/templates.rs
index a9887497b..d5b5b0d55 100644
--- a/crates/defguard_mail/src/templates.rs
+++ b/crates/defguard_mail/src/templates.rs
@@ -6,6 +6,7 @@ use defguard_common::{
     db::models::{Session, Settings, user::MFAMethod},
     types::UrlParseError,
 };
+use pulldown_cmark::{Event, HeadingLevel, Parser, Tag, TagEnd, html};
 use reqwest::Url;
 use serde::Serialize;
 use serde_json::Value;
@@ -191,6 +192,110 @@ pub async fn desktop_start_mail(
     Ok(())
 }
 
+/// Iterator that enforces the supported subset of CommonMark
+/// so that only elements with a corresponding rule in `MARKDOWN_EMAIL_STYLES`
+/// are emitted to the HTML renderer.
+struct EmailEventFilter<'a, I: Iterator<Item = Event<'a>>> {
+    iter: I,
+    skip_depth: usize,
+}
+
+impl<'a, I: Iterator<Item = Event<'a>>> EmailEventFilter<'a, I> {
+    fn new(iter: I) -> Self {
+        Self {
+            iter,
+            skip_depth: 0,
+        }
+    }
+}
+
+impl<'a, I: Iterator<Item = Event<'a>>> Iterator for EmailEventFilter<'a, I> {
+    type Item = Event<'a>;
+
+    fn next(&mut self) -> Option<Self::Item> {
+        loop {
+            let event = self.iter.next()?;
+
+            // Inside a skipped block: track nesting depth and discard.
+            if self.skip_depth > 0 {
+                match &event {
+                    Event::Start(_) => self.skip_depth += 1,
+                    Event::End(_) => self.skip_depth -= 1,
+                    _ => {}
+                }
+                continue;
+            }
+
+            return Some(match event {
+                // block elements without styles: skip entirely
+                Event::Start(Tag::BlockQuote(_) | Tag::List(Some(_)) | Tag::CodeBlock(_)) => {
+                    self.skip_depth = 1;
+                    continue;
+                }
+
+                // inline elements without styles: drop the tag, keep text
+                Event::Start(Tag::Emphasis | Tag::Strikethrough)
+                | Event::End(TagEnd::Emphasis | TagEnd::Strikethrough) => continue,
+
+                // inline code: render as plain text
+                Event::Code(text) => Event::Text(text),
+
+                // headings: degrade h3-h6 to h2
+                Event::Start(Tag::Heading {
+                    level,
+                    id,
+                    classes,
+                    attrs,
+                }) if !matches!(level, HeadingLevel::H1 | HeadingLevel::H2) => {
+                    Event::Start(Tag::Heading {
+                        level: HeadingLevel::H2,
+                        id,
+                        classes,
+                        attrs,
+                    })
+                }
+                Event::End(TagEnd::Heading(level))
+                    if !matches!(level, HeadingLevel::H1 | HeadingLevel::H2) =>
+                {
+                    Event::End(TagEnd::Heading(HeadingLevel::H2))
+                }
+
+                // raw HTML and horizontal rules: strip
+                Event::Html(_) | Event::InlineHtml(_) | Event::Rule => continue,
+
+                other => other,
+            });
+        }
+    }
+}
+
+static MARKDOWN_EMAIL_STYLES: &str = r#"
+h1 { font-size: 24px; font-weight: 600; color: #141517; line-height: 32px; font-family: Geist, Arial, sans-serif; margin: 0 0 8px 0; }
+h2 { font-size: 16px; font-weight: 400; color: #4A5059; line-height: 24px; font-family: Geist, Arial, sans-serif; margin: 0 0 8px 0; }
+p { font-size: 14px; font-weight: 400; color: #4A5059; line-height: 20px; font-family: Geist, Arial, sans-serif; margin: 0 0 12px 0; }
+a { color: #3961DB; text-decoration: underline; font-size: 14px; line-height: 20px; }
+ul { list-style: disc; margin: 0 0 12px 0; padding: 0; }
+li { font-size: 14px; font-weight: 400; color: #4A5059; line-height: 20px; font-family: Geist, Arial, sans-serif; margin-left: 21px; }
+strong, b { font-weight: 600; }
+"#;
+
+/// Renders a markdown string to an inline-styled HTML fragment.
+/// Only elements with a corresponding rule in `MARKDOWN_EMAIL_STYLES` are
+/// rendered; everything else is stripped or degraded (see `EmailEventFilter`).
+pub fn markdown_to_html(content: &str) -> String {
+    let parser = EmailEventFilter::new(Parser::new(content));
+    let mut raw_html = String::new();
+    html::push_html(&mut raw_html, parser);
+
+    match css_inline::inline_fragment(&raw_html, MARKDOWN_EMAIL_STYLES) {
+        Ok(styled) => styled,
+        Err(err) => {
+            warn!("Failed to apply inline styles to markdown HTML: {err}");
+            raw_html
+        }
+    }
+}
+
 /// Welcome message sent when activating an account through enrollment.
 /// Its content is stored in markdown, so it's parsed into HTML and plain text.
 pub fn enrollment_welcome_mail(
@@ -203,10 +308,7 @@ pub fn enrollment_welcome_mail(
         get_base_tera_mjml(Context::new(), None, ip_address, device_info)?;
 
     debug!("Render welcome mail template for user enrollment");
-    // Convert content to HTML.
-    let parser = pulldown_cmark::Parser::new(content);
-    let mut html_output = String::new();
-    pulldown_cmark::html::push_html(&mut html_output, parser);
+    let html_output = markdown_to_html(content);
 
     context.insert("welcome_message_content", &html_output);
 
diff --git a/crates/defguard_mail/src/tests.rs b/crates/defguard_mail/src/tests.rs
index b857e395e..24044c6f6 100644
--- a/crates/defguard_mail/src/tests.rs
+++ b/crates/defguard_mail/src/tests.rs
@@ -394,6 +394,260 @@ fn send_enrollment_welcome_mail(_: PgPoolOptions, options: PgConnectOptions) {
     tokio::time::sleep(Duration::from_secs(2)).await;
 }
 
+mod markdown_to_html {
+    use crate::templates::markdown_to_html;
+
+    fn has_tag(html: &str, tag: &str) -> bool {
+        html.contains(&format!("<{tag}"))
+    }
+
+    #[test]
+    fn h1_has_inline_style() {
+        let html = markdown_to_html("# Title");
+        assert!(has_tag(&html, "h1"), "h1 tag missing: {html}");
+        assert!(html.contains("font-size: 24px"), "h1 font-size: {html}");
+        assert!(html.contains("#141517"), "h1 color: {html}");
+        assert!(html.contains("font-weight: 600"), "h1 font-weight: {html}");
+        assert!(html.contains("Title"), "h1 text missing: {html}");
+    }
+
+    #[test]
+    fn h2_has_inline_style() {
+        let html = markdown_to_html("## Subtitle");
+        assert!(has_tag(&html, "h2"), "h2 tag missing: {html}");
+        assert!(html.contains("font-size: 16px"), "h2 font-size: {html}");
+        assert!(html.contains("#4A5059"), "h2 color: {html}");
+        assert!(html.contains("Subtitle"), "h2 text missing: {html}");
+    }
+
+    #[test]
+    fn paragraph_has_inline_style() {
+        let html = markdown_to_html("Hello world");
+        assert!(has_tag(&html, "p"), "p tag missing: {html}");
+        assert!(html.contains("font-size: 14px"), "p font-size: {html}");
+        assert!(html.contains("#4A5059"), "p color: {html}");
+        assert!(html.contains("Hello world"), "p text missing: {html}");
+    }
+
+    #[test]
+    fn bold_has_inline_style() {
+        let html = markdown_to_html("**important**");
+        assert!(has_tag(&html, "strong"), "strong tag missing: {html}");
+        assert!(
+            html.contains("font-weight: 600"),
+            "strong font-weight: {html}"
+        );
+        assert!(html.contains("important"), "bold text missing: {html}");
+    }
+
+    #[test]
+    fn link_has_inline_style_and_href() {
+        let html = markdown_to_html("[click here](https://example.com)");
+        assert!(has_tag(&html, "a"), "a tag missing: {html}");
+        assert!(html.contains("https://example.com"), "href missing: {html}");
+        assert!(html.contains("#3961DB"), "a color: {html}");
+        assert!(html.contains("click here"), "link text missing: {html}");
+    }
+
+    #[test]
+    fn unordered_list_has_inline_styles() {
+        let html = markdown_to_html("- Alpha\n- Beta");
+        assert!(has_tag(&html, "ul"), "ul tag missing: {html}");
+        assert!(has_tag(&html, "li"), "li tag missing: {html}");
+        assert!(html.contains("Alpha"), "first item text missing: {html}");
+        assert!(html.contains("Beta"), "second item text missing: {html}");
+        assert!(html.contains("font-size: 14px"), "li font-size: {html}");
+    }
+
+    #[test]
+    fn h3_through_h6_are_demoted_to_h2() {
+        for (level, marker) in [(3, "###"), (4, "####"), (5, "#####"), (6, "######")] {
+            let html = markdown_to_html(&format!("{marker} Heading {level}"));
+            assert!(
+                has_tag(&html, "h2"),
+                "h{level} must be demoted to h2: {html}"
+            );
+            assert!(
+                !has_tag(&html, &format!("h{level}")),
+                "h{level} must not appear: {html}"
+            );
+            assert!(
+                html.contains(&format!("Heading {level}")),
+                "h{level} text must be preserved: {html}"
+            );
+        }
+    }
+
+    #[test]
+    fn horizontal_rule_is_stripped() {
+        let html = markdown_to_html("---");
+        assert!(!has_tag(&html, "hr"), "hr must be stripped: {html}");
+    }
+
+    #[test]
+    fn blockquote_is_stripped() {
+        let html = markdown_to_html("> confidential");
+        assert!(
+            !has_tag(&html, "blockquote"),
+            "blockquote tag must be stripped: {html}"
+        );
+        assert!(
+            !html.contains("confidential"),
+            "blockquote content must not appear: {html}"
+        );
+    }
+
+    #[test]
+    fn ordered_list_is_stripped() {
+        let html = markdown_to_html("1. First\n2. Second");
+        assert!(!has_tag(&html, "ol"), "ol tag must be stripped: {html}");
+        assert!(
+            !html.contains("First"),
+            "ordered list content must not appear: {html}"
+        );
+    }
+
+    #[test]
+    fn fenced_code_block_is_stripped() {
+        let html = markdown_to_html("```rust\nlet x = 1;\n```");
+        assert!(!has_tag(&html, "pre"), "pre tag must be stripped: {html}");
+        assert!(!has_tag(&html, "code"), "code tag must be stripped: {html}");
+        assert!(
+            !html.contains("let x"),
+            "code block content must not appear: {html}"
+        );
+    }
+
+    #[test]
+    fn indented_code_block_is_stripped() {
+        let html = markdown_to_html("    indented block");
+        assert!(!has_tag(&html, "pre"), "pre tag must be stripped: {html}");
+        assert!(
+            !html.contains("indented block"),
+            "indented code block content must not appear: {html}"
+        );
+    }
+
+    #[test]
+    fn inline_code_rendered_as_plain_text() {
+        let html = markdown_to_html("`fn main()`");
+        assert!(!has_tag(&html, "code"), "code tag must be stripped: {html}");
+        assert!(
+            html.contains("fn main()"),
+            "inline code text must be preserved: {html}"
+        );
+    }
+
+    #[test]
+    fn raw_block_html_is_stripped() {
+        let html = markdown_to_html("<div class=\"x\">content</div>");
+        assert!(
+            !html.contains("<div"),
+            "raw HTML div must be stripped: {html}"
+        );
+    }
+
+    #[test]
+    fn script_tag_is_stripped() {
+        // <script> opens an HTML block consuming its whole line, so "Safe paragraph"
+        // must be in a separate paragraph to survive stripping.
+        let html = markdown_to_html("<script>alert('xss')</script>\n\nSafe paragraph.");
+        assert!(
+            !html.contains("<script"),
+            "script tag must be stripped: {html}"
+        );
+        assert!(
+            html.contains("Safe paragraph"),
+            "surrounding text must survive: {html}"
+        );
+    }
+
+    #[test]
+    fn inline_html_is_stripped() {
+        let html = markdown_to_html("before <b>inline</b> after");
+        assert!(
+            !html.contains("<b>"),
+            "inline HTML b tag must be stripped: {html}"
+        );
+    }
+
+    #[test]
+    fn nested_unsupported_blocks_are_fully_stripped() {
+        let html = markdown_to_html("> 1. nested item");
+        assert!(
+            !has_tag(&html, "blockquote"),
+            "blockquote must be stripped: {html}"
+        );
+        assert!(!has_tag(&html, "ol"), "ol must be stripped: {html}");
+        assert!(
+            !html.contains("nested item"),
+            "nested content must not appear: {html}"
+        );
+    }
+
+    #[test]
+    fn bold_and_italic_in_same_paragraph() {
+        let html = markdown_to_html("**bold** and *italic* together");
+        assert!(has_tag(&html, "strong"), "strong must be present: {html}");
+        assert!(!has_tag(&html, "em"), "em must be stripped: {html}");
+        assert!(html.contains("bold"), "bold text must survive: {html}");
+        assert!(html.contains("italic"), "italic text must survive: {html}");
+    }
+
+    #[test]
+    fn bold_inside_link() {
+        let html = markdown_to_html("[**bold link**](https://example.com)");
+        assert!(has_tag(&html, "a"), "a tag missing: {html}");
+        assert!(has_tag(&html, "strong"), "strong inside a missing: {html}");
+        assert!(html.contains("https://example.com"), "href missing: {html}");
+        assert!(html.contains("bold link"), "link text missing: {html}");
+    }
+
+    #[test]
+    fn multiple_paragraphs_are_each_styled() {
+        let html = markdown_to_html("First paragraph.\n\nSecond paragraph.");
+        assert!(
+            html.matches("<p").count() >= 2,
+            "expected at least two p tags: {html}"
+        );
+        assert!(html.contains("First paragraph"), "first p text: {html}");
+        assert!(html.contains("Second paragraph"), "second p text: {html}");
+    }
+
+    #[test]
+    fn hr_surrounded_by_paragraphs_is_stripped() {
+        let html = markdown_to_html("Before.\n\n---\n\nAfter.");
+        assert!(!has_tag(&html, "hr"), "hr must be stripped: {html}");
+        assert!(
+            html.contains("Before"),
+            "text before hr must survive: {html}"
+        );
+        assert!(html.contains("After"), "text after hr must survive: {html}");
+    }
+
+    #[test]
+    fn empty_input_produces_no_tags() {
+        let html = markdown_to_html("");
+        assert!(
+            html.trim().is_empty(),
+            "empty input must produce no output: {html}"
+        );
+    }
+
+    #[test]
+    fn plain_text_is_wrapped_in_paragraph() {
+        let html = markdown_to_html("Just some text.");
+        assert!(
+            has_tag(&html, "p"),
+            "plain text must be wrapped in p: {html}"
+        );
+        assert!(
+            html.contains("Just some text"),
+            "text must be preserved: {html}"
+        );
+    }
+}
+
 #[test]
 fn test_mfa_configured_subject_totp() {
     // TOTP
diff --git a/crates/defguard_mail/templates/enrollment-welcome.mjml b/crates/defguard_mail/templates/enrollment-welcome.mjml
index 0339017b1..984a9d3e3 100644
--- a/crates/defguard_mail/templates/enrollment-welcome.mjml
+++ b/crates/defguard_mail/templates/enrollment-welcome.mjml
@@ -5,9 +5,7 @@
 <mj-section>
   <mj-column mj-class="s-3xl">
     <mj-text>
-      <p>
-        {{ welcome_message_content }}
-      </p>
+      {{ welcome_message_content }}
     </mj-text>
   </mj-column>
 </mj-section>
diff --git a/crates/defguard_proxy_manager/src/servers/enrollment.rs b/crates/defguard_proxy_manager/src/servers/enrollment.rs
index d950e0dc9..ccf461536 100644
--- a/crates/defguard_proxy_manager/src/servers/enrollment.rs
+++ b/crates/defguard_proxy_manager/src/servers/enrollment.rs
@@ -369,10 +369,16 @@ impl EnrollmentServer {
         }
 
         debug!("Try to send welcome email...");
-        enrollment
+        match enrollment
             .send_welcome_email(conn, user, ip_address, device_info)
-            .await?;
-        info!("Welcome email sent to {} at {}", user.username, user.email);
+            .await
+        {
+            Ok(()) => info!("Welcome email sent to {} at {}", user.username, user.email),
+            Err(err) => warn!(
+                "Failed to send enrollment welcome email to {} at {}: {err}.",
+                user.username, user.email
+            ),
+        }
 
         Ok(())
     }
diff --git a/crates/defguard_proxy_manager/src/tests/proxy_manager/handler/polling.rs b/crates/defguard_proxy_manager/src/tests/proxy_manager/handler/polling.rs
index 726f87b36..51192362a 100644
--- a/crates/defguard_proxy_manager/src/tests/proxy_manager/handler/polling.rs
+++ b/crates/defguard_proxy_manager/src/tests/proxy_manager/handler/polling.rs
@@ -1,9 +1,8 @@
-use sqlx::postgres::{PgConnectOptions, PgPoolOptions};
-
 use defguard_proto::{
     client_types::InstanceInfoRequest,
     proxy::{CoreRequest, core_request, core_response},
 };
+use sqlx::postgres::{PgConnectOptions, PgPoolOptions};
 
 use super::support::{
     assert_error_response, clear_test_license, complete_proxy_handshake, create_device_for_user,
diff --git a/web/messages/en/settings.json b/web/messages/en/settings.json
index 9e41e895f..8066c6d7c 100644
--- a/web/messages/en/settings.json
+++ b/web/messages/en/settings.json
@@ -121,18 +121,11 @@
   "settings_enrollment_template_help_admin_phone": "phone number of the administrator who initiated the enrollment process",
   "settings_enrollment_template_help_admin_email": "email of the administrator who initiated the enrollment process",
   "settings_enrollment_template_help_defguard_url": "internal Defguard URL (your Defguard instance address)",
+  "settings_enrollment_template_help_defguard_version": "Defguard version",
   "settings_enrollment_template_help_markdown_headings": "Create headings.",
-  "settings_enrollment_template_help_markdown_italic": "Italic text.",
   "settings_enrollment_template_help_markdown_bold": "Bold text.",
-  "settings_enrollment_template_help_markdown_bold_italic": "Bold and italic.",
-  "settings_enrollment_template_help_markdown_blockquote": "Blockquote.",
-  "settings_enrollment_template_help_markdown_lists": "Lists (unordered or ordered).",
-  "settings_enrollment_template_help_markdown_inline_code": "Inline code.",
-  "settings_enrollment_template_help_markdown_code_block": "Code block.",
-  "settings_enrollment_template_help_markdown_horizontal_line": "Horizontal line.",
+  "settings_enrollment_template_help_markdown_lists": "Unordered list.",
   "settings_enrollment_template_help_markdown_link": "Link.",
-  "settings_enrollment_template_help_markdown_tables": "Create tables.",
-  "settings_enrollment_template_help_markdown_escape": "Escape special characters.",
   "settings_enrollment_section_duration_title": "Enrollment session duration",
   "settings_enrollment_section_duration_description": "Configure the expiration time of the unique token sent to a newly added user. This token is used to activate the account, and in this section administrators can control how long the token remains valid.",
   "settings_enrollment_label_session_expires_in": "Enrollment session expires in",
diff --git a/web/src/pages/EnrollmentPage/tabs/MessageTemplatesTab.tsx b/web/src/pages/EnrollmentPage/tabs/MessageTemplatesTab.tsx
index 67ec820ea..638f7712a 100644
--- a/web/src/pages/EnrollmentPage/tabs/MessageTemplatesTab.tsx
+++ b/web/src/pages/EnrollmentPage/tabs/MessageTemplatesTab.tsx
@@ -30,21 +30,14 @@ const messageTemplatesHelpVariables = [
   ['{{ admin_phone }}', m.settings_enrollment_template_help_admin_phone()],
   ['{{ admin_email }}', m.settings_enrollment_template_help_admin_email()],
   ['{{ defguard_url }}', m.settings_enrollment_template_help_defguard_url()],
+  ['{{ defguard_version }}', m.settings_enrollment_template_help_defguard_version()],
 ] as const;
 
 const messageTemplatesHelpMarkdown = [
-  ['#, ##, ###', m.settings_enrollment_template_help_markdown_headings(), 'medium'],
-  ['*text*', m.settings_enrollment_template_help_markdown_italic()],
+  ['#, ##', m.settings_enrollment_template_help_markdown_headings(), 'medium'],
   ['**text**', m.settings_enrollment_template_help_markdown_bold()],
-  ['***text***', m.settings_enrollment_template_help_markdown_bold_italic()],
-  ['> text', m.settings_enrollment_template_help_markdown_blockquote()],
-  ['- item or 1. item', m.settings_enrollment_template_help_markdown_lists()],
-  ['`code`', m.settings_enrollment_template_help_markdown_inline_code()],
-  ['```code```', m.settings_enrollment_template_help_markdown_code_block()],
-  ['***', m.settings_enrollment_template_help_markdown_horizontal_line()],
+  ['- item', m.settings_enrollment_template_help_markdown_lists()],
   ['[text](url)', m.settings_enrollment_template_help_markdown_link()],
-  ['| and ---', m.settings_enrollment_template_help_markdown_tables()],
-  ['\\', m.settings_enrollment_template_help_markdown_escape()],
 ] as const;
 
 const messageTemplatesFormSchema = z.object({