diff --git a/src/io/perun.clj b/src/io/perun.clj
index 0311681f..20c022c1 100644
--- a/src/io/perun.clj
+++ b/src/io/perun.clj
@@ -9,7 +9,8 @@
             [clojure.string :as string]
             [clojure.edn :as edn]
             [io.perun.core :as perun]
-            [io.perun.meta :as pm]))
+            [io.perun.meta :as pm]
+            [clojure.string :as str]))
 
 (def ^:private ^:deps global-deps
   '[])
@@ -458,18 +459,57 @@
                    :meta meta
                    :cmd-opts cmd-opts))))
 
-(def ^:private ^:deps asciidoctor-deps
-  '[[org.clojure/tools.namespace "0.3.0-alpha3"]
-    [org.asciidoctor/asciidoctorj "1.5.4"]])
+(defn extensions->regex
+  "Helper function to convert a sequence of extensions to a regex"
+  [extensions]
+  {:pre [map (fn [ext] (assert (.startsWith ext ".")) extensions)]}
+  (->> extensions
+       (map (fn [ext] (str/escape ext {\. "\\."})))
+       (str/join "|")
+       (#(str ".*(?:" % ")$"))
+       re-pattern))
+
+(def ^:private +collect-images-defaults+
+  {:extensions [".png" ".svg" ".jpg"]})
+
+(deftask collect-images
+  "Collect images from a directory"
+  [d img-dir    IMGDIR     str   "the image directory"
+   e extensions EXTENSIONS [str] "extensions of files to include"]
+  (let [{:keys [img-dir extensions] :as options} (merge +collect-images-defaults+ *opts*)
+        include-regex                            (extensions->regex extensions)]
+    (boot/with-pre-wrap fileset
+      (-> fileset
+          (boot/add-resource (clojure.java.io/file img-dir) :include #{include-regex})
+          (boot/commit!)))))
+
+(defn asciidoctor-deps [diagram?]
+  (let [adoc-deps    '[[clj-time "0.14.0"]
+                       [org.clojure/tools.namespace "0.3.0-alpha3"]
+                       [org.asciidoctor/asciidoctorj "1.5.4"]]
+        diagram-deps '[[org.asciidoctor/asciidoctorj-diagram "1.5.0"]]]
+    (-> (if diagram?
+          (into adoc-deps diagram-deps)
+          adoc-deps)
+        (with-meta {:private true :deps true}))))
 
 (def ^:private +asciidoctor-defaults+
   {:out-dir    "public"
    :out-ext    ".html"
    :filterer   identity
+   :images     false
    :extensions [".ad" ".asc" ".adoc" ".asciidoc"]
    :meta       {:original     true
                 :include-rss  true
-                :include-atom true}})
+                :include-atom true}
+   :safe       1})
+
+(defn strip-nil-vals
+  "Helper function for removing nil values, to ensure proper merge of maps"
+  [m]
+  (->> m
+       (remove #(nil? (second %)))
+       (into {})))
 
 (deftask asciidoctor*
   "Parse asciidoc files using Asciidoctor
@@ -479,17 +519,23 @@
   [d out-dir    OUTDIR     str   "the output directory"
    _ filterer   FILTER     code  "predicate to use for selecting entries (default: `identity`)"
    e extensions EXTENSIONS [str] "extensions of files to process"
-   m meta       META       edn   "metadata to set on each entry"]
-  (let [pod     (create-pod asciidoctor-deps)
-        options (merge +asciidoctor-defaults+ *opts*)]
-    (content-task
-     {:render-form-fn (fn [data] `(io.perun.asciidoctor/process-asciidoctor ~data))
-      :paths-fn       #(content-paths % options)
-      :passthru-fn    content-passthru
-      :task-name      "asciidoctor"
-      :tracer         :io.perun/asciidoctor
-      :rm-originals   true
-      :pod            pod})))
+   _ diagram               bool  "if `true`, generate images from inline text using asciidoctor-diagram"
+   m meta       META       edn   "metadata to set on each entry"
+   s safe       SAFE       int   "security level (default: 1)"]
+  (let [{:keys [diagram safe out-dir] :as options} (merge +asciidoctor-defaults+ (strip-nil-vals *opts*))
+        pod                                        (create-pod (asciidoctor-deps diagram))
+        img-dir                                    (.getPath (boot/tmp-dir!))]
+    (comp (content-task
+           {:render-form-fn (fn [data] `(io.perun.asciidoctor/process-asciidoctor ~out-dir ~img-dir ~diagram ~safe ~data))
+            :paths-fn       #(content-paths % options)
+            :passthru-fn    content-passthru
+            :task-name      "asciidoctor"
+            :tracer         :io.perun/asciidoctor
+            :rm-originals   true
+            :pod            pod})
+          (if diagram
+            (collect-images :img-dir img-dir)
+            identity))))
 
 (deftask asciidoctor
   "Parse asciidoc files with yaml front matter using Asciidoctor
@@ -499,13 +545,17 @@
   [d out-dir    OUTDIR     str   "the output directory"
    _ filterer   FILTER     code  "predicate to use for selecting entries (default: `identity`)"
    e extensions EXTENSIONS [str] "extensions of files to process"
-   m meta       META       edn   "metadata to set on each entry"]
+   _ diagram               bool  "if `true`, generate images from inline text using asciidoctor-diagram"
+   m meta       META       edn   "metadata to set on each entry"
+   s safe       SAFE       int   "security level (default: 1)"]
   (let [{:keys [out-dir filterer extensions meta]} (merge +asciidoctor-defaults+ *opts*)]
     (comp (yaml-metadata :filterer filterer :extensions extensions)
           (asciidoctor* :out-dir    out-dir
                         :filterer   filterer
+                        :diagram    diagram
                         :extensions extensions
-                        :meta       meta))))
+                        :meta       meta
+                        :safe       safe))))
 
 (deftask global-metadata
   "Read global metadata from `perun.base.edn` or configured file.
diff --git a/src/io/perun/asciidoctor.clj b/src/io/perun/asciidoctor.clj
index 02c52529..8b1a1d94 100644
--- a/src/io/perun/asciidoctor.clj
+++ b/src/io/perun/asciidoctor.clj
@@ -1,16 +1,101 @@
 (ns io.perun.asciidoctor
   (:require [io.perun.core :as perun]
-            [clojure.java.io :as io])
+            [clj-time.coerce :as tc]
+            [clj-time.format :as tf]
+            [clojure.java.io :as io]
+            [clojure.string :as str])
   (:import [org.asciidoctor Asciidoctor Asciidoctor$Factory]))
 
-(def container
-  (Asciidoctor$Factory/create ""))
+(defn keywords->names
+  "Converts a map with keywords to a map with named keys. Only handles the top
+   level of any nested structure."
+  [m]
+  (reduce-kv #(assoc %1 (name %2) %3) {} m))
 
-(defn asciidoctor-to-html [file-content]
-  (.convert container file-content {}))
+(defn names->keywords
+  "Converts a map with named keys to a map with keywords. Only handles the top
+   level of any nested structure."
+  [m]
+  (reduce-kv #(assoc %1 (keyword %2) %3) {} m))
 
-(defn process-asciidoctor [{:keys [entry]}]
+(defn container
+  "Creates a new Asciidoctor container, with or without the
+  `asciidoctor-diagram` library."
+  [diagram]
+  (doto (Asciidoctor$Factory/create "")
+    (.requireLibraries (if diagram
+                         '("asciidoctor-diagram")
+                         '()))))
+
+(defn meta->attributes
+  "Takes the Perun meta and converts it to a collection of attributes, which can
+  be handed to the AsciidoctorJ process."
+  [meta]
+  (-> meta
+      keywords->names
+      (java.util.HashMap.)))
+
+(defn parse-date
+  "Tries to parse a date string into a DateTime object"
+  [date]
+  (when date
+    (if-let [parsed (tc/to-date date)]
+      parsed
+      (perun/report-info "asciidoctor" "failed to parse date %s" date))))
+
+(defn attributes->meta
+  "Add duplicate entries for the metadata keys gathered from the AsciidoctorJ
+  parsing using keys that adhere to the Perun specification of keys. The native
+  AsciidoctorJ keys are still available."
+  [attributes]
+  (let [meta (names->keywords (into {} attributes))]
+    (merge meta
+           {:author-email   (:email     meta)
+            :title          (:doctitle  meta)
+            :date-published (parse-date (:revdate meta))})))
+
+(defn protect-meta
+  "Strip keywords from metadata that are being used by Perun to properly
+  function."
+  [meta]
+  (dissoc meta
+          :canonical-url :content :extension :filename :full-path :parent-path
+          :path :permalink :short-filename :slug))
+
+(defn options
+  "Create an options object"
+  [safe attributes outdir]
+  {:pre [(number? safe)]}
+  {"attributes" (if attributes
+                  attributes
+                  (java.util.HashMap.))
+   "safe"       (int safe)
+   "base_dir"   outdir})
+
+(defn parse-file-metadata
+  "Processes the asciidoctor content and extracts all the attributes."
+  [container adoc-content options]
+  (->> (.readDocumentStructure container adoc-content options)
+       (.getHeader)
+       (.getAttributes)
+       attributes->meta
+       protect-meta))
+
+(defn asciidoctor-to-html [container file-content options]
+  (.convert container file-content options))
+
+(defn strip-trailing-slash
+  [path]
+  (str/replace path "/^" ""))
+
+(defn process-asciidoctor [out-dir img-dir diagram safe {:keys [entry]}]
   (perun/report-debug "asciidoctor" "processing asciidoctor" (:filename entry))
-  (let [file-content (-> entry :full-path io/file slurp)
-        html         (asciidoctor-to-html file-content)]
-    (assoc entry :rendered html)))
+  (let [outdir       (str/replace (str/join "/" [img-dir out-dir (:parent-path entry)]) "/^" "")
+        _            (.mkdirs (clojure.java.io/file outdir))
+        file-content (-> entry :full-path io/file slurp)
+        attributes   (meta->attributes (assoc entry :outdir outdir))
+        opts         (options safe attributes outdir)
+        cont         (container diagram)
+        html         (asciidoctor-to-html cont file-content opts)
+        meta         (parse-file-metadata cont file-content opts)]
+    (merge (assoc entry :rendered html) meta)))
diff --git a/src/io/perun/yaml.clj b/src/io/perun/yaml.clj
index 3ce30b72..0d562959 100644
--- a/src/io/perun/yaml.clj
+++ b/src/io/perun/yaml.clj
@@ -7,7 +7,7 @@
   (:import [flatland.ordered.map OrderedMap]
            [flatland.ordered.set OrderedSet]))
 
-(def ^:dynamic *yaml-head* #"---\r?\n")
+(def ^:dynamic *yaml-head* #"(?<=^|\n)---\r?\n")
 
 (defn substr-between
   "Find string that is nested in between two strings. Return first match.