diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
index 31c5005cd53d..1ce4cf240a9c 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
@@ -426,7 +426,7 @@ public static String replaceMediaFileWithUrlInGutenbergPost(@NonNull String post
                     .notNullStr(Utils.escapeQuotes(mediaFile.getFileURL()));
             MediaUploadCompletionProcessor processor = new MediaUploadCompletionProcessor(localMediaId, mediaFile,
                     siteUrl);
-            postContent = processor.processPost(postContent);
+            postContent = processor.processContent(postContent);
         }
         return postContent;
     }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessor.java
index eccb6b37d43c..80129877df69 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessor.java
@@ -1,5 +1,8 @@
 package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
 
+import com.google.gson.JsonObject;
+import com.google.gson.JsonParser;
+
 import org.jsoup.Jsoup;
 import org.jsoup.nodes.Document;
 import org.jsoup.nodes.Document.OutputSettings;
@@ -7,7 +10,8 @@
 import org.wordpress.android.util.helpers.MediaFile;
 
 import java.util.regex.Matcher;
-import java.util.regex.Pattern;
+
+import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaUploadCompletionProcessorPatterns.PATTERN_BLOCK_CAPTURES;
 
 /**
  * Abstract class to be extended for each enumerated {@link MediaBlockType}.
@@ -27,11 +31,12 @@ abstract class BlockProcessor {
     String mRemoteId;
     String mRemoteUrl;
 
-    private Pattern mBlockPattern;
-    private String mHeaderComment;
-    private String mBlockContent;
+    private String mBlockName;
+    private JsonObject mJsonAttributes;
+    private Document mBlockContentDocument;
     private String mClosingComment;
 
+
     /**
      * @param localId The local media id that needs replacement
      * @param mediaFile The mediaFile containing the remote id and remote url
@@ -40,51 +45,38 @@ abstract class BlockProcessor {
         mLocalId = localId;
         mRemoteId = mediaFile.getMediaId();
         mRemoteUrl = org.wordpress.android.util.StringUtils.notNullStr(Utils.escapeQuotes(mediaFile.getFileURL()));
-        mBlockPattern = Pattern.compile(String.format(getBlockPatternTemplate(), localId), Pattern.DOTALL);
     }
 
-    // TODO: consider processing block header JSON in a more robust way (current processing uses RexEx)
-    /**
-     * @param block The raw block contents of the block to be matched
-     * @return A {@link Matcher} to extract block contents and splice the header with a remote id. The matcher has the
-     * following capture groups:
-     *
-     * <ol>
-     * <li>Block header before id</li>
-     * <li>The localId (to be replaced)</li>
-     * <li>Block header after id</li>
-     * <li>Block contents</li>
-     * <li>Block closing comment and any following characters</li>
-     * </ol>
-     */
-    Matcher getMatcherForBlock(String block) {
-        return mBlockPattern.matcher(block);
+    private JsonObject parseJson(String blockJson) {
+        JsonParser parser = new JsonParser();
+        return parser.parse(blockJson).getAsJsonObject();
+    }
+
+    private Document parseHTML(String blockContent) {
+        // create document from block content
+        Document document = Jsoup.parse(blockContent);
+        document.outputSettings(OUTPUT_SETTINGS);
+        return document;
     }
 
-    boolean matchAndSpliceBlockHeader(String block) {
-        Matcher matcher = getMatcherForBlock(block);
+    private boolean splitBlock(String block) {
+        Matcher captures = PATTERN_BLOCK_CAPTURES.matcher(block);
 
-        boolean matchFound = matcher.find();
+        boolean capturesFound = captures.find();
 
-        if (matchFound) {
-            mHeaderComment = new StringBuilder()
-                    .append(matcher.group(1))
-                    .append(mRemoteId) // here we substitute remote id in place of the local id
-                    .append(matcher.group(3))
-                    .toString();
-            mBlockContent = matcher.group(4);
-            mClosingComment = matcher.group(5);
+        if (capturesFound) {
+            mBlockName = captures.group(1);
+            mJsonAttributes = parseJson(captures.group(2));
+            mBlockContentDocument = parseHTML(captures.group(3));
+            mClosingComment = captures.group(4);
+            return true;
         } else {
-            mHeaderComment = null;
-            mBlockContent = null;
+            mBlockName = null;
+            mJsonAttributes = null;
+            mBlockContentDocument = null;
             mClosingComment = null;
+            return false;
         }
-
-        return matchFound;
-    }
-
-    String getHeaderComment() {
-        return mHeaderComment;
     }
 
     /**
@@ -94,46 +86,28 @@ String getHeaderComment() {
      * @param block The raw block contents
      * @return A string containing content with ids and urls replaced
      */
-     String processBlock(String block) {
-         if (matchAndSpliceBlockHeader(block)) {
-             // create document from block content
-             Document document = Jsoup.parse(mBlockContent);
-             document.outputSettings(OUTPUT_SETTINGS);
-
-             if (processBlockContentDocument(document)) {
-                 // return injected block
-                 return new StringBuilder()
-                         .append(getHeaderComment())
-                         .append(document.body().html()) // parser output
-                         .append(mClosingComment)
-                         .toString();
-             }
-         }
-
-         // leave block unchanged
-         return block;
-     }
-
-    /**
-     * All concrete implementations must implement this method to return a regex pattern template for the particular
-     * block type.<br>
-     * <br>
-     * The pattern template should contain a format specifier for the local id that needs to be matched and
-     * replaced in the block header, and the format specifier should be within its own capture group, e.g. `(%1$s)`.<br>
-     * <br>
-     * The pattern template should result in a matcher with the following capture groups:
-     *
-     * <ol>
-     * <li>Block header before id</li>
-     * <li>The format specifier for the local id (to be replaced by the local id when generating the pattern)</li>
-     * <li>Block header after id</li>
-     * <li>Block contents</li>
-     * <li>Block closing comment and any following characters</li>
-     * </ol>
-     *
-     * @return String with the regex pattern template
-     */
-    abstract String getBlockPatternTemplate();
+    String processBlock(String block) {
+        if (splitBlock(block)) {
+            if (processBlockJsonAttributes(mJsonAttributes)) {
+                if (processBlockContentDocument(mBlockContentDocument)) {
+                    // return injected block
+                    return new StringBuilder()
+                            .append("<!-- wp:")
+                            .append(mBlockName)
+                            .append(" ")
+                            .append(mJsonAttributes) // json parser output
+                            .append(" -->\n")
+                            .append(mBlockContentDocument.body().html()) // HTML parser output
+                            .append(mClosingComment)
+                            .toString();
+                }
+            } else {
+                return processInnerBlock(block); // delegate to inner blocks if needed
+            }
+        }
+        // leave block unchanged
+        return block;
+    }
 
     /**
      * All concrete implementations must implement this method for the particular block type. The document represents
@@ -146,4 +120,33 @@ String processBlock(String block) {
      * @return A boolean value indicating whether or not the block contents should be replaced
      */
     abstract boolean processBlockContentDocument(Document document);
+
+    /**
+     * All concrete implementations must implement this method for the particular block type. The jsonAttributes object
+     * is a {@link JsonObject} parsed from the block header attributes. This object can be used to check for a match,
+     * and can be directly mutated if necessary.<br>
+     * <br>
+     * This method should return true to indicate success. Returning false will result in the block contents being
+     * unmodified.
+     *
+     * @param jsonAttributes the attributes object used to check for a match with the local id, and mutated if necessary
+     * @return
+     */
+    abstract boolean processBlockJsonAttributes(JsonObject jsonAttributes);
+
+    /**
+     * This method can be optionally overriden by concrete implementations to delegate further processing via recursion
+     * when {@link BlockProcessor#processBlockJsonAttributes(JsonObject)} returns false (i.e. the block did not match
+     * the local id being replaced). This is useful for implementing mutual recursion with
+     * {@link MediaUploadCompletionProcessor#processContent(String)} for block types that have media-containing blocks
+     * within their inner content.<br>
+     * <br>
+     * The default implementation provided is a NOOP that leaves the content of the block unchanged.
+     *
+     * @param block The raw block contents
+     * @return A string containing content with ids and urls replaced
+     */
+    String processInnerBlock(String block) {
+        return block;
+    }
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessorFactory.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessorFactory.java
index 1c0d8e60528b..b33568c3c850 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessorFactory.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/BlockProcessorFactory.java
@@ -5,19 +5,22 @@
 import java.util.HashMap;
 import java.util.Map;
 
+import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaBlockType.COVER;
 import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaBlockType.GALLERY;
 import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaBlockType.IMAGE;
 import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaBlockType.MEDIA_TEXT;
 import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaBlockType.VIDEO;
 
 class BlockProcessorFactory {
+    private final MediaUploadCompletionProcessor mMediaUploadCompletionProcessor;
     private final Map<MediaBlockType, BlockProcessor> mMediaBlockTypeBlockProcessorMap;
 
     /**
      * This factory initializes block processors for all media block types and provides a method to retrieve a block
      * processor instance for a given block type.
      */
-    BlockProcessorFactory() {
+    BlockProcessorFactory(MediaUploadCompletionProcessor mediaUploadCompletionProcessor) {
+        mMediaUploadCompletionProcessor = mediaUploadCompletionProcessor;
         mMediaBlockTypeBlockProcessorMap = new HashMap<>();
     }
 
@@ -32,6 +35,8 @@ BlockProcessorFactory init(String localId, MediaFile mediaFile, String siteUrl)
         mMediaBlockTypeBlockProcessorMap.put(VIDEO, new VideoBlockProcessor(localId, mediaFile));
         mMediaBlockTypeBlockProcessorMap.put(MEDIA_TEXT, new MediaTextBlockProcessor(localId, mediaFile));
         mMediaBlockTypeBlockProcessorMap.put(GALLERY, new GalleryBlockProcessor(localId, mediaFile, siteUrl));
+        mMediaBlockTypeBlockProcessorMap.put(COVER, new CoverBlockProcessor(localId, mediaFile,
+                mMediaUploadCompletionProcessor));
 
         return this;
     }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessor.java
new file mode 100644
index 000000000000..f5cc3e18b6bc
--- /dev/null
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessor.java
@@ -0,0 +1,79 @@
+package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
+
+import com.google.gson.JsonObject;
+
+import org.jsoup.nodes.Document;
+import org.jsoup.nodes.Element;
+import org.wordpress.android.util.helpers.MediaFile;
+
+import java.util.regex.Matcher;
+import java.util.regex.Pattern;
+
+public class CoverBlockProcessor extends BlockProcessor {
+    /**
+     * Template pattern used to match and splice cover inner blocks
+     */
+    private static final Pattern PATTERN_COVER_INNER = Pattern.compile(new StringBuilder()
+                    .append("(^.*?<div class=\"wp-block-cover__inner-container\">\\s*)")
+                    .append("(.*)") // inner block contents
+                    .append("(\\s*</div>\\s*</div>\\s*<!-- /wp:cover -->.*)").toString(), Pattern.DOTALL);
+
+    /**
+     * Pattern to match background-image url in cover block html content
+     */
+    private static final Pattern PATTERN_BACKGROUND_IMAGE_URL = Pattern.compile(
+            "background-image:\\s*url\\([^\\)]+\\)");
+
+    private final MediaUploadCompletionProcessor mMediaUploadCompletionProcessor;
+
+    public CoverBlockProcessor(String localId, MediaFile mediaFile,
+                               MediaUploadCompletionProcessor mediaUploadCompletionProcessor) {
+        super(localId, mediaFile);
+        mMediaUploadCompletionProcessor = mediaUploadCompletionProcessor;
+    }
+
+    @Override String processInnerBlock(String block) {
+        Matcher innerMatcher = PATTERN_COVER_INNER.matcher(block);
+        boolean innerCapturesFound = innerMatcher.find();
+
+        // process inner contents recursively
+        if (innerCapturesFound) {
+            String innerProcessed = mMediaUploadCompletionProcessor.processContent(innerMatcher.group(2)); //
+            return new StringBuilder()
+                    .append(innerMatcher.group(1))
+                    .append(innerProcessed)
+                    .append(innerMatcher.group(3))
+                    .toString();
+        }
+
+        return block;
+    }
+
+    @Override boolean processBlockJsonAttributes(JsonObject jsonAttributes) {
+        if (jsonAttributes.get("id").getAsInt() == Integer.parseInt(mLocalId, 10)) {
+            jsonAttributes.addProperty("id", Integer.parseInt(mRemoteId, 10));
+            jsonAttributes.addProperty("url", mRemoteUrl);
+            return true;
+        }
+
+        return false;
+    }
+
+    @Override boolean processBlockContentDocument(Document document) {
+        // select cover block div
+        Element targetDiv = document.select(".wp-block-cover").first();
+
+        // if a match is found, proceed with replacement
+        if (targetDiv != null) {
+            // replace background-image url in style attribute
+            String style = PATTERN_BACKGROUND_IMAGE_URL.matcher(targetDiv.attr("style"))
+                    .replaceFirst(String.format("background-image:url(%1$s)", mRemoteUrl));
+            targetDiv.attr("style", style);
+
+            // return injected block
+            return true;
+        }
+
+        return false;
+    }
+}
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/GalleryBlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/GalleryBlockProcessor.java
index 4d5c25a9c226..59d7f8363036 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/GalleryBlockProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/GalleryBlockProcessor.java
@@ -1,38 +1,17 @@
 package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
 
+import com.google.gson.JsonArray;
+import com.google.gson.JsonElement;
+import com.google.gson.JsonObject;
+import com.google.gson.JsonPrimitive;
+
 import org.jsoup.nodes.Document;
 import org.jsoup.nodes.Element;
 import org.wordpress.android.util.helpers.MediaFile;
 
-import java.util.regex.Matcher;
-import java.util.regex.Pattern;
-
 public class GalleryBlockProcessor extends BlockProcessor {
-    /**
-     * Template pattern used to match and splice gallery blocks
-     */
-    private static final String PATTERN_TEMPLATE_GALLERY = "(<!-- wp:gallery \\{[^\\}]*\"ids\":\\[(?:\"?\\d+\"?,)*)"
-                                                           + "(\"?%1$s\"?)" // local id must match to be replaced
-                                                           + "([,\\]][^>]*-->\n?)" // rest of header
-                                                           + "(.*)" // block contents
-                                                           + "(<!-- /wp:gallery -->\n?)"; // closing comment
-
-
-    /**
-     * A {@link Pattern} to match and capture gallery linkTo property from block header
-     *
-     * <ol>
-     *     <li>Block header before linkTo property</li>
-     *     <li>The linkTo property</li>
-     *     <li>Block header after linkTo property</li>
-     * </ol>
-     */
-    public static final Pattern PATTERN_GALLERY_LINK_TO = Pattern.compile("(<!-- wp:gallery \\{[^\\}]*\"linkTo\":\")"
-                                                                          + "([^\"]*)" // linkTo value
-                                                                          + "([\"][^>]*-->\n?)"); // rest of header
-
-
     private String mAttachmentPageUrl;
+    private String mLinkTo;
 
     /**
      * Query selector for selecting the img element from gallery which needs processing
@@ -49,10 +28,6 @@ public GalleryBlockProcessor(String localId, MediaFile mediaFile, String siteUrl
         mAttachmentPageUrl = mediaFile.getAttachmentPageURL(siteUrl);
     }
 
-    @Override String getBlockPatternTemplate() {
-        return PATTERN_TEMPLATE_GALLERY;
-    }
-
     @Override boolean processBlockContentDocument(Document document) {
         // select image element with our local id
         Element targetImg = document.select(mGalleryImageQuerySelector).first();
@@ -69,15 +44,10 @@ public GalleryBlockProcessor(String localId, MediaFile mediaFile, String siteUrl
             targetImg.removeClass("wp-image-" + mLocalId);
             targetImg.addClass("wp-image-" + mRemoteId);
 
-            // check for linkTo property
-            Matcher linkToMatcher = PATTERN_GALLERY_LINK_TO.matcher(getHeaderComment());
-
             // set parent anchor href if necessary
             Element parent = targetImg.parent();
-            if (parent != null && parent.is("a") && linkToMatcher.find()) {
-                String linkToValue = linkToMatcher.group(2);
-
-                switch (linkToValue) {
+            if (parent != null && parent.is("a") && mLinkTo != null) {
+                switch (mLinkTo) {
                     case "media":
                         parent.attr("href", mRemoteUrl);
                         break;
@@ -95,4 +65,19 @@ public GalleryBlockProcessor(String localId, MediaFile mediaFile, String siteUrl
 
         return false;
     }
+
+    @Override boolean processBlockJsonAttributes(JsonObject jsonAttributes) {
+        JsonArray ids = jsonAttributes.getAsJsonArray("ids");
+        JsonElement linkTo = jsonAttributes.get("linkTo");
+        if (linkTo != null) {
+            mLinkTo = linkTo.getAsString();
+        }
+        for (int i = 0; i < ids.size(); i++) {
+            if (ids.get(i).getAsString().equals(mLocalId)) {
+                ids.set(i, new JsonPrimitive(Integer.parseInt(mRemoteId, 10)));
+                return true;
+            }
+        }
+        return false;
+    }
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/ImageBlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/ImageBlockProcessor.java
index 650a92ca148a..fc2dd197060f 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/ImageBlockProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/ImageBlockProcessor.java
@@ -1,27 +1,16 @@
 package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
 
+import com.google.gson.JsonObject;
+
 import org.jsoup.nodes.Document;
 import org.jsoup.nodes.Element;
 import org.wordpress.android.util.helpers.MediaFile;
 
 public class ImageBlockProcessor extends BlockProcessor {
-    /**
-     * Template pattern used to match and splice image blocks
-     */
-    private static final String PATTERN_TEMPLATE_IMAGE = "(<!-- wp:image \\{[^\\}]*\"id\":)" // block
-                                                         + "(%1$s)" // local id must match to be replaced
-                                                         + "([,\\}][^>]*-->\n?)" // rest of header
-                                                         + "(.*)" // block contents
-                                                         + "(<!-- /wp:image -->\n?)"; // closing comment
-
     public ImageBlockProcessor(String localId, MediaFile mediaFile) {
         super(localId, mediaFile);
     }
 
-    @Override String getBlockPatternTemplate() {
-        return PATTERN_TEMPLATE_IMAGE;
-    }
-
     @Override boolean processBlockContentDocument(Document document) {
         // select image element with our local id
         Element targetImg = document.select("img").first();
@@ -40,4 +29,13 @@ public ImageBlockProcessor(String localId, MediaFile mediaFile) {
 
         return false;
     }
+
+    @Override boolean processBlockJsonAttributes(JsonObject jsonAttributes) {
+        if (jsonAttributes.get("id").getAsString().equals(mLocalId)) {
+            jsonAttributes.addProperty("id", Integer.parseInt(mRemoteId));
+            return true;
+        }
+
+        return false;
+    }
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaBlockType.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaBlockType.java
index fd3fa6a1de10..7de0bf67305b 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaBlockType.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaBlockType.java
@@ -3,6 +3,8 @@
 import org.apache.commons.lang3.StringUtils;
 
 import java.util.Arrays;
+import java.util.HashMap;
+import java.util.Map;
 import java.util.regex.Matcher;
 import java.util.regex.Pattern;
 
@@ -12,7 +14,26 @@ enum MediaBlockType {
     IMAGE("image"),
     VIDEO("video"),
     MEDIA_TEXT("media-text"),
-    GALLERY("gallery");
+    GALLERY("gallery"),
+    COVER("cover");
+
+    private static final Map<String, MediaBlockType> MAP = new HashMap<>();
+    private static final String MATCHING_GROUP;
+    private static final Pattern PATTERN_MEDIA_BLOCK_TYPES;
+
+    static {
+        for (MediaBlockType type : values()) {
+            MAP.put(type.mName, type);
+        }
+
+        MATCHING_GROUP = StringUtils.join(Arrays.asList(MediaBlockType.values()), "|");
+
+        PATTERN_MEDIA_BLOCK_TYPES = Pattern.compile(new StringBuilder()
+                .append(PATTERN_BLOCK_PREFIX)
+                .append(MATCHING_GROUP)
+                .append(")")
+                .toString());
+    }
 
     private final String mName;
 
@@ -25,12 +46,7 @@ public String toString() {
     }
 
     static MediaBlockType fromString(String blockType) {
-        for (MediaBlockType mediaBlockType : MediaBlockType.values()) {
-            if (mediaBlockType.mName.equals(blockType)) {
-                return mediaBlockType;
-            }
-        }
-        return null;
+        return MAP.get(blockType);
     }
 
     /**
@@ -38,7 +54,7 @@ static MediaBlockType fromString(String blockType) {
      * regex capturing group pattern)
      */
     static String getMatchingGroup() {
-        return StringUtils.join(Arrays.asList(MediaBlockType.values()), "|");
+        return MATCHING_GROUP;
     }
 
     /**
@@ -48,12 +64,7 @@ static String getMatchingGroup() {
      * @return The media block type or null if no match is found
      */
     static MediaBlockType detectBlockType(String block) {
-        final Pattern pattern = Pattern.compile(new StringBuilder()
-                .append(PATTERN_BLOCK_PREFIX)
-                .append(MediaBlockType.getMatchingGroup())
-                .append(")")
-                .toString());
-        Matcher matcher = pattern.matcher(block);
+        Matcher matcher = PATTERN_MEDIA_BLOCK_TYPES.matcher(block);
 
         if (matcher.find()) {
             return MediaBlockType.fromString(matcher.group(1));
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaTextBlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaTextBlockProcessor.java
index 588f630ddd02..558eaa12536d 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaTextBlockProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaTextBlockProcessor.java
@@ -1,27 +1,16 @@
 package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
 
+import com.google.gson.JsonObject;
+
 import org.jsoup.nodes.Document;
 import org.jsoup.nodes.Element;
 import org.wordpress.android.util.helpers.MediaFile;
 
 public class MediaTextBlockProcessor extends BlockProcessor {
-    /**
-     * Template pattern used to match and splice media-text blocks
-     */
-    private static final String PATTERN_TEMPLATE_MEDIA_TEXT = "(<!-- wp:media-text \\{[^\\}]*\"mediaId\":)" // block
-                                                              + "(%1$s)" // local id must match to be replaced
-                                                              + "([,\\}][^>]*-->\n?)" // rest of header
-                                                              + "(.*)" // block contents
-                                                              + "(<!-- /wp:media-text -->\n?)"; // closing comment
-
     public MediaTextBlockProcessor(String localId, MediaFile mediaFile) {
         super(localId, mediaFile);
     }
 
-    @Override String getBlockPatternTemplate() {
-        return PATTERN_TEMPLATE_MEDIA_TEXT;
-    }
-
     @Override boolean processBlockContentDocument(Document document) {
         // select image element with our local id
         Element targetImg = document.select("img").first();
@@ -53,4 +42,13 @@ public MediaTextBlockProcessor(String localId, MediaFile mediaFile) {
 
         return false;
     }
+
+    @Override boolean processBlockJsonAttributes(JsonObject jsonAttributes) {
+        if (jsonAttributes.get("mediaId").getAsString().equals(mLocalId)) {
+            jsonAttributes.addProperty("mediaId", Integer.parseInt(mRemoteId));
+            return true;
+        }
+
+        return false;
+    }
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessor.java
index f741dc7a820d..bd75608a9e24 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessor.java
@@ -3,8 +3,10 @@
 import org.wordpress.android.util.helpers.MediaFile;
 
 import java.util.regex.Matcher;
+import java.util.regex.Pattern;
 
-import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaUploadCompletionProcessorPatterns.PATTERN_BLOCK;
+import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaUploadCompletionProcessorPatterns.PATTERN_BLOCK_HEADER;
+import static org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaUploadCompletionProcessorPatterns.PATTERN_TEMPLATE_BLOCK_BOUNDARY;
 
 public class MediaUploadCompletionProcessor {
     private final BlockProcessorFactory mBlockProcessorFactory;
@@ -18,34 +20,49 @@ public class MediaUploadCompletionProcessor {
      * @param siteUrl The site url - used to generate the attachmentPage url
      */
     public MediaUploadCompletionProcessor(String localId, MediaFile mediaFile, String siteUrl) {
-        mBlockProcessorFactory = new BlockProcessorFactory()
+        mBlockProcessorFactory = new BlockProcessorFactory(this)
                 .init(localId, mediaFile, siteUrl);
     }
 
     /**
-     * Processes a post to replace the local ids and local urls of media with remote ids and remote urls. This matches
-     * media-containing blocks and delegates further processing to {@link #processBlock(String)}
+     * Processes content to replace the local ids and local urls of media with remote ids and remote urls. This method
+     * delineates block boundaries for media-containing blocks and delegates further processing via itself and / or
+     * {@link #processBlock(String)}, via direct and mutual recursion, respectively.
      *
-     * @param postContent The post content to be processed
-     * @return A string containing the processed post, or the original content if no match was found
+     * @param content The content to be processed
+     * @return A string containing the processed content, or the original content if no match was found
      */
-    public String processPost(String postContent) {
-        Matcher matcher = PATTERN_BLOCK.matcher(postContent);
-        StringBuilder result = new StringBuilder();
+    public String processContent(String content) {
+        Matcher headerMatcher = PATTERN_BLOCK_HEADER.matcher(content);
 
-        int position = 0;
+        int positionBlockStart, positionBlockEnd = content.length();
 
-        while (matcher.find()) {
-            result.append(postContent.substring(position, matcher.start()));
-            result.append(processBlock(matcher.group()));
-            position = matcher.end();
-        }
+        if (headerMatcher.find()) {
+            positionBlockStart = headerMatcher.start();
+            String blockType = headerMatcher.group(1);
+            Matcher blockBoundaryMatcher = Pattern.compile(String.format(PATTERN_TEMPLATE_BLOCK_BOUNDARY, blockType),
+                    Pattern.DOTALL).matcher(content.substring(headerMatcher.end()));
 
-        result.append(postContent.substring(position));
+            int nestLevel = 1;
 
-        return result.toString();
-    }
+            while (0 < nestLevel && blockBoundaryMatcher.find()) {
+                if (blockBoundaryMatcher.group(1).equals("/")) {
+                    positionBlockEnd = headerMatcher.end() + blockBoundaryMatcher.end();
+                    nestLevel--;
+                } else {
+                    nestLevel++;
+                }
+            }
 
+            return new StringBuilder()
+                    .append(content.substring(0, positionBlockStart))
+                    .append(processBlock(content.substring(positionBlockStart, positionBlockEnd)))
+                    .append(processContent(content.substring(positionBlockEnd)))
+                    .toString();
+        } else {
+            return content;
+        }
+    }
 
     /**
      * Processes a media block returning a raw content replacement string
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatterns.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatterns.java
index 157730a9aad5..643fada1f527 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatterns.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatterns.java
@@ -3,17 +3,40 @@
 import java.util.regex.Pattern;
 
 public class MediaUploadCompletionProcessorPatterns {
-    // TODO: these patterns can be DRYed up after implementing JSON handling for the block header
     public static final String PATTERN_BLOCK_PREFIX = "<!-- wp:(";
-    public static final String PATTERN_BLOCK_SUFFIX = "<!-- /wp:\\1 -->";
 
     /**
-     * A {@link Pattern} to match Gutenberg media-containing blocks with a capture group for the block type
+     * A {@link Pattern} to match headers for Gutenberg media-containing blocks with a capture group for the block type
      */
-    public static final Pattern PATTERN_BLOCK = Pattern.compile(new StringBuilder()
+    public static final Pattern PATTERN_BLOCK_HEADER = Pattern.compile(new StringBuilder()
             .append(PATTERN_BLOCK_PREFIX)
             .append(MediaBlockType.getMatchingGroup())
-            .append(").*?")
-            .append(PATTERN_BLOCK_SUFFIX)
+            .append(").*? -->\n?")
+            .toString(), Pattern.DOTALL);
+
+    /**
+     * A pattern template to match the block boundaries of a specific Gutenberg block type with a capture group to
+     * identify the match as either the beginning or end of a block: group(1) == "/" for the end of a block
+     */
+    public static final String PATTERN_TEMPLATE_BLOCK_BOUNDARY = "<!-- (/?)wp:%1$s.*? -->\n?";
+
+    /**
+     * A {@link Pattern} to match Gutenberg media-containing blocks with the following capture groups:
+     *
+     * <ol>
+     * <li>Block type</li>
+     * <li>Block json attributes</li>
+     * <li>Block html content</li>
+     * <li>Block closing comment and any following characters</li>
+     * </ol>
+     *
+     */
+    public static final Pattern PATTERN_BLOCK_CAPTURES = Pattern.compile(new StringBuilder()
+            .append(PATTERN_BLOCK_PREFIX) // start-of-group: block type
+            .append(MediaBlockType.getMatchingGroup())
+            .append(")") // end-of-group: block type
+            .append(" (\\{.*?\\}) -->\n?") // group: block header json
+            .append("(.*)") // group: html content
+            .append("(<!-- /wp:\\1 -->.*)") // group: closing-comment (name must match group 1: block type)
             .toString(), Pattern.DOTALL);
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/VideoBlockProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/VideoBlockProcessor.java
index 1f188f253fef..ae91d130dbdf 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/VideoBlockProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/VideoBlockProcessor.java
@@ -1,27 +1,16 @@
 package org.wordpress.android.ui.posts.mediauploadcompletionprocessors;
 
+import com.google.gson.JsonObject;
+
 import org.jsoup.nodes.Document;
 import org.jsoup.nodes.Element;
 import org.wordpress.android.util.helpers.MediaFile;
 
 public class VideoBlockProcessor extends BlockProcessor {
-    /**
-     * Template pattern used to match and splice video blocks
-     */
-    private static final String PATTERN_TEMPLATE_VIDEO = "(<!-- wp:video \\{[^\\}]*\"id\":)" // block
-                                                         + "(%1$s)" // local id must match to be replaced
-                                                         + "([,\\}][^>]*-->\n?)" // rest of header
-                                                         + "(.*)" // block contents
-                                                         + "(<!-- /wp:video -->\n?)"; // closing comment
-
     public VideoBlockProcessor(String localId, MediaFile mediaFile) {
         super(localId, mediaFile);
     }
 
-    @Override String getBlockPatternTemplate() {
-        return PATTERN_TEMPLATE_VIDEO;
-    }
-
     @Override boolean processBlockContentDocument(Document document) {
         // select video element with our local id
         Element targetVideo = document.select("video").first();
@@ -37,4 +26,13 @@ public VideoBlockProcessor(String localId, MediaFile mediaFile) {
 
         return false;
     }
+
+    @Override boolean processBlockJsonAttributes(JsonObject jsonAttributes) {
+        if (jsonAttributes.get("id").getAsString().equals(mLocalId)) {
+            jsonAttributes.addProperty("id", Integer.parseInt(mRemoteId));
+            return true;
+        }
+
+        return false;
+    }
 }
diff --git a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessorTest.kt b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessorTest.kt
new file mode 100644
index 000000000000..c67dfbcab422
--- /dev/null
+++ b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/CoverBlockProcessorTest.kt
@@ -0,0 +1,63 @@
+package org.wordpress.android.ui.posts.mediauploadcompletionprocessors
+
+import com.nhaarman.mockitokotlin2.any
+import com.nhaarman.mockitokotlin2.mock
+import com.nhaarman.mockitokotlin2.whenever
+import org.assertj.core.api.Assertions
+import org.junit.Test
+import org.junit.Before
+
+import org.wordpress.android.util.helpers.MediaFile
+
+class CoverBlockProcessorTest {
+    private val mediaFile: MediaFile = mock()
+    private val mediaUploadCompletionProcessor: MediaUploadCompletionProcessor = mock()
+    private lateinit var processor: CoverBlockProcessor
+
+    @Before
+    fun before() {
+        whenever(mediaFile.mediaId).thenReturn(TestContent.remoteMediaId)
+        whenever(mediaFile.fileURL).thenReturn(TestContent.remoteImageUrl)
+        processor = CoverBlockProcessor(TestContent.localMediaId, mediaFile, mediaUploadCompletionProcessor)
+    }
+
+    @Test
+    fun `processBlock replaces temporary local id and url for cover block`() {
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlock)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.newCoverBlock)
+    }
+
+    @Test
+    fun `processBlock works with nested image blocks`() {
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlockWithNestedImageBlock)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.newCoverBlockWithNestedImageBlock)
+    }
+
+    @Test
+    fun `processBlock does not process inner nested cover blocks`() {
+        whenever(mediaUploadCompletionProcessor.processContent(any())).thenReturn(TestContent.oldCoverBlock + "\n  ")
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlockWithNestedCoverBlockInner)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.oldCoverBlockWithNestedCoverBlockInner)
+    }
+
+    @Test
+    fun `processBlock works with outer nested cover blocks`() {
+        whenever(mediaFile.mediaId).thenReturn(TestContent.remoteMediaId2)
+        whenever(mediaFile.fileURL).thenReturn(TestContent.remoteImageUrl2)
+        processor = CoverBlockProcessor(TestContent.localMediaId2, mediaFile, mediaUploadCompletionProcessor)
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlockWithNestedCoverBlockOuter)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.newCoverBlockWithNestedCoverBlockOuter)
+    }
+
+    @Test
+    fun `processBlock works with different inline style order`() {
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlockDifferentStyleOrder)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.newCoverBlockDifferentStyleOrder)
+    }
+
+    @Test
+    fun `processBlock works with a space in inline styles`() {
+        val processedBlock = processor.processBlock(TestContent.oldCoverBlockStyleOrderWithSpace)
+        Assertions.assertThat(processedBlock).isEqualTo(TestContent.newCoverBlockStyleOrderWithoutSpace)
+    }
+}
diff --git a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatternsTest.kt b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatternsTest.kt
new file mode 100644
index 000000000000..87f2b2c407c4
--- /dev/null
+++ b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorPatternsTest.kt
@@ -0,0 +1,51 @@
+package org.wordpress.android.ui.posts.mediauploadcompletionprocessors
+
+import org.assertj.core.api.Assertions
+import org.junit.Test
+import org.wordpress.android.ui.posts.mediauploadcompletionprocessors.MediaUploadCompletionProcessorPatterns.PATTERN_BLOCK_CAPTURES
+
+const val blockType = "image"
+const val blockJson = """{"url":"file:///image.png","id":123,someObject:{a:1,b:2},someArray:[1,2,3]}"""
+const val blockHTML = """<div class="wp-block-cover has-background-dim" style="background-image:url(file:///image.png)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+"""
+const val blockHeader = """<!-- wp:$blockType $blockJson -->"""
+const val blockClosingComment = """<!-- /wp:$blockType -->"""
+const val rawBlock = """$blockHeader
+$blockHTML
+$blockClosingComment"""
+const val nestedRawBlock = """$blockHeader
+<div class="wp-block-cover has-background-dim" style="background-image:url(file:///image.png)">
+  <div class="wp-block-cover__inner-container">
+  $rawBlock
+  </div>
+</div>
+$blockClosingComment
+"""
+
+class MediaUploadCompletionProcessorPatternsTest {
+    @Test
+    fun `PATTERN_BLOCK_CAPTURES captures the block type`() {
+        val matcher = PATTERN_BLOCK_CAPTURES.matcher(rawBlock)
+        val outcome = matcher.find()
+        Assertions.assertThat(outcome).isEqualTo(true)
+        Assertions.assertThat(matcher.group(1)).isEqualTo(blockType)
+    }
+    @Test
+    fun `PATTERN_BLOCK_CAPTURES captures the block header json`() {
+        val matcher = PATTERN_BLOCK_CAPTURES.matcher(rawBlock)
+        Assertions.assertThat(matcher.find()).isEqualTo(true)
+        Assertions.assertThat(matcher.group(2)).isEqualTo(blockJson)
+    }
+    @Test
+    fun `PATTERN_BLOCK_CAPTURES captures the block content`() {
+        val matcher = PATTERN_BLOCK_CAPTURES.matcher(rawBlock)
+        Assertions.assertThat(matcher.find()).isEqualTo(true)
+        Assertions.assertThat(matcher.group(3)).isEqualTo(blockHTML + "\n")
+    }
+}
diff --git a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorTest.kt b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorTest.kt
index fd6b52b30389..5d8a29bfd706 100644
--- a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorTest.kt
+++ b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/MediaUploadCompletionProcessorTest.kt
@@ -26,7 +26,7 @@ class MediaUploadCompletionProcessorTest {
 
     @Test
     fun `processPost splices id and url for an image block`() {
-        val blocks = processor.processPost(TestContent.oldPostImage)
+        val blocks = processor.processContent(TestContent.oldPostImage)
         Assertions.assertThat(blocks).isEqualTo(TestContent.newPostImage)
     }
 
@@ -34,19 +34,52 @@ class MediaUploadCompletionProcessorTest {
     fun `processPost splices id and url for a video block`() {
         whenever(mediaFile.fileURL).thenReturn(TestContent.remoteVideoUrl)
         processor = MediaUploadCompletionProcessor(TestContent.localMediaId, mediaFile, TestContent.siteUrl)
-        val blocks = processor.processPost(TestContent.oldPostVideo)
+        val blocks = processor.processContent(TestContent.oldPostVideo)
         Assertions.assertThat(blocks).isEqualTo(TestContent.newPostVideo)
     }
 
     @Test
     fun `processPost splices id and url for a media-text block`() {
-        val blocks = processor.processPost(TestContent.oldPostMediaText)
+        val blocks = processor.processContent(TestContent.oldPostMediaText)
         Assertions.assertThat(blocks).isEqualTo(TestContent.newPostMediaText)
     }
 
     @Test
     fun `processPost splices id and url for a gallery block`() {
-        val blocks = processor.processPost(TestContent.oldPostGallery)
+        val blocks = processor.processContent(TestContent.oldPostGallery)
         Assertions.assertThat(blocks).isEqualTo(TestContent.newPostGallery)
     }
+
+    @Test
+    fun `processPost splices id and url for a cover block`() {
+        val blocks = processor.processContent(TestContent.oldPostCover)
+        Assertions.assertThat(blocks).isEqualTo(TestContent.newPostCover)
+    }
+
+    @Test
+    fun `processPost works for nested inner cover blocks`() {
+        val blocks = processor.processContent(TestContent.oldCoverBlockWithNestedCoverBlockInner)
+        Assertions.assertThat(blocks).isEqualTo(TestContent.newCoverBlockWithNestedCoverBlockInner)
+    }
+
+    @Test
+    fun `processPost works for nested outer cover blocks`() {
+        whenever(mediaFile.mediaId).thenReturn(TestContent.remoteMediaId2)
+        whenever(mediaFile.fileURL).thenReturn(TestContent.remoteImageUrl2)
+        processor = MediaUploadCompletionProcessor(TestContent.localMediaId2, mediaFile, TestContent.siteUrl)
+        val blocks = processor.processContent(TestContent.oldCoverBlockWithNestedCoverBlockOuter)
+        Assertions.assertThat(blocks).isEqualTo(TestContent.newCoverBlockWithNestedCoverBlockOuter)
+    }
+
+    @Test
+    fun `processPost works for image blocks nested within a cover block`() {
+        val processedContent = processor.processContent(TestContent.oldImageBlockNestedInCoverBlock)
+        Assertions.assertThat(processedContent).isEqualTo(TestContent.newImageBlockNestedInCoverBlock)
+    }
+
+    @Test
+    fun `processPost leaves malformed cover block unchanged`() {
+        val processedContent = processor.processContent(TestContent.malformedCoverBlock)
+        Assertions.assertThat(processedContent).isEqualTo(TestContent.malformedCoverBlock)
+    }
 }
diff --git a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/TestContent.kt b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/TestContent.kt
index 2a6a02dd9147..985bcc976ea8 100644
--- a/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/TestContent.kt
+++ b/WordPress/src/test/java/org/wordpress/android/ui/posts/mediauploadcompletionprocessors/TestContent.kt
@@ -5,18 +5,21 @@ package org.wordpress.android.ui.posts.mediauploadcompletionprocessors
 object TestContent {
     const val siteUrl = "https://wordpress.org"
     private const val localImageUrl = "file://Screenshot-1-1.png"
+    private const val localImageUrl2 = "file://Screenshot-1-2.png"
     const val remoteImageUrl = "https://onetwoonetwothisisjustatesthome.files.wordpress.com/2019/11/pexels-photo-1671668.jpg"
+    const val remoteImageUrl2 = "https://onetwoonetwothisisjustatesthome.files.wordpress.com/2019/12/img_20191202_094944-19.jpg"
     private const val remoteImageUrlBlogLink = "http://onetwoonetwothisisjustatest.home.blog/pexels-photo-1671668/"
     private const val remoteImageUrlWithSize = "https://onetwoonetwothisisjustatesthome.files.wordpress.com/2019/11/pexels-photo-1671668.jpg?w=1024"
-    private const val remoteImageUrl2 = "https://onetwoonetwothisisjustatesthome.files.wordpress.com/2019/12/img_20191202_094944-19.jpg"
     private const val remoteImageUrl2BlogLink = "http://onetwoonetwothisisjustatest.home.blog/?attachment_id=369"
     private const val remoteImageUrl2WithSize = "https://onetwoonetwothisisjustatesthome.files.wordpress.com/2019/12/img_20191202_094944-19.jpg?w=768"
     private const val localVideoUrl = "file://local-video.mov"
     const val remoteVideoUrl = "https://videos.files.wordpress.com/qeJFeNa2/macintosh-plus-floral-shoppe-02-e383aae382b5e38395e383a9e383b3e382af420-e78fbee4bba3e381aee382b3e383b3e38394e383a5e383bc-1_hd.mp4"
     const val localMediaId = "112"
+    const val localMediaId2 = "113"
     private const val collidingPrefixMediaId = "${localMediaId}42"
     private const val collidingSuffixMediaId = "42${localMediaId}"
     const val remoteMediaId = "97629"
+    const val remoteMediaId2 = "97630"
     const val attachmentPageUrl = "https://wordpress.org?p=${remoteMediaId}"
 
     const val oldImageBlock = """<!-- wp:image {"id":${localMediaId},"align":"full"} -->
@@ -357,6 +360,143 @@ object TestContent {
   </ul>
 </figure>
 <!-- /wp:gallery -->
+"""
+
+    const val oldCoverBlock = """<!-- wp:cover {"url":"$localImageUrl","id":$localMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+
+    const val newCoverBlock = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val oldCoverBlockWithNestedImageBlock = """<!-- wp:cover {"url":"$localImageUrl","id":$localMediaId} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl)">
+  <div class="wp-block-cover__inner-container">
+  $newImageBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val newCoverBlockWithNestedImageBlock = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+  $newImageBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val oldCoverBlockWithNestedCoverBlockOuter = """<!-- wp:cover {"url":"$localImageUrl2","id":$localMediaId2} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl2)">
+  <div class="wp-block-cover__inner-container">
+  $oldCoverBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val newCoverBlockWithNestedCoverBlockOuter = """<!-- wp:cover {"url":"$remoteImageUrl2","id":$remoteMediaId2} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl2)">
+  <div class="wp-block-cover__inner-container">
+  $oldCoverBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val oldCoverBlockWithNestedCoverBlockInner = """<!-- wp:cover {"url":"$localImageUrl2","id":$localMediaId2} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl2)">
+  <div class="wp-block-cover__inner-container">
+  $oldCoverBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val newCoverBlockWithNestedCoverBlockInner = """<!-- wp:cover {"url":"$localImageUrl2","id":$localMediaId2} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl2)">
+  <div class="wp-block-cover__inner-container">
+  $newCoverBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val oldImageBlockNestedInCoverBlock = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+  $oldImageBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val newImageBlockNestedInCoverBlock = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+  $newImageBlock
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val malformedCoverBlock = """<!-- wp:cover {"url":"$localImageUrl","id":$localMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($localImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+"""
+    const val oldCoverBlockDifferentStyleOrder = """<!-- wp:cover {"url":"$localImageUrl","id":$localMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="color:black;background-image:url($localImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+
+    const val newCoverBlockDifferentStyleOrder = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="color:black;background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+    const val oldCoverBlockStyleOrderWithSpace = """<!-- wp:cover {"url":"$localImageUrl","id":$localMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="background-image: url($localImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
+"""
+
+    const val newCoverBlockStyleOrderWithoutSpace = """<!-- wp:cover {"url":"$remoteImageUrl","id":$remoteMediaId,"someOtherAttribute":5} -->
+<div class="wp-block-cover has-background-dim" style="background-image:url($remoteImageUrl)">
+  <div class="wp-block-cover__inner-container">
+    <!-- wp:paragraph {"align":"center","placeholder":"Write title…"} -->
+    <p class="has-text-align-center"></p>
+    <!-- /wp:paragraph -->
+  </div>
+</div>
+<!-- /wp:cover -->
 """
 
     const val oldPostImage = paragraphBlock + oldImageBlock + newVideoBlock + newMediaTextBlock + newGalleryBlock
@@ -367,4 +507,6 @@ object TestContent {
     const val newPostMediaText = paragraphBlock + newImageBlock + newVideoBlock + newMediaTextBlock + newGalleryBlock
     const val oldPostGallery = paragraphBlock + newImageBlock + newVideoBlock + newMediaTextBlock + oldGalleryBlock
     const val newPostGallery = paragraphBlock + newImageBlock + newVideoBlock + newMediaTextBlock + newGalleryBlock
+    const val oldPostCover = paragraphBlock + newImageBlock + oldCoverBlock + newMediaTextBlock + oldGalleryBlock
+    const val newPostCover = paragraphBlock + newImageBlock + newCoverBlock + newMediaTextBlock + newGalleryBlock
 }
diff --git a/libs/gutenberg-mobile b/libs/gutenberg-mobile
index 6906be56ace3..6d7a9952ea96 160000
--- a/libs/gutenberg-mobile
+++ b/libs/gutenberg-mobile
@@ -1 +1 @@
-Subproject commit 6906be56ace31186ded1df0b65b9ea34fe2aaf34
+Subproject commit 6d7a9952ea964eb9d3eb79f41463e2465fba6585