diff --git a/streaming/index.js b/streaming/index.js
index a40d8739fb..4d0937bf8a 100644
--- a/streaming/index.js
+++ b/streaming/index.js
@@ -634,29 +634,39 @@ const startWorker = async (workerId) => {
 
     log.verbose(req.requestId, `Starting stream from ${ids.join(', ')} for ${accountId}`);
 
-    // Currently message is of type string, soon it'll be Record<string, any>
+    const transmit = (event, payload) => {
+      // TODO: Replace "string"-based delete payloads with object payloads:
+      const encodedPayload = typeof payload === 'object' ? JSON.stringify(payload) : payload;
+
+      log.silly(req.requestId, `Transmitting for ${accountId}: ${event} ${encodedPayload}`);
+      output(event, encodedPayload);
+    };
+
+    // The listener used to process each message off the redis subscription,
+    // message here is an object with an `event` and `payload` property. Some
+    // events also include a queued_at value, but this is being removed shortly.
     const listener = message => {
-      const { event, payload, queued_at } = message;
+      const { event, payload } = message;
 
-      const transmit = (payload) => {
-        const now = new Date().getTime();
-        const delta = now - queued_at;
-        const encodedPayload = typeof payload === 'object' ? JSON.stringify(payload) : payload;
-
-        log.silly(req.requestId, `Transmitting for ${accountId}: ${event} ${encodedPayload} Delay: ${delta}ms`);
-        output(event, encodedPayload);
-      };
-
-      // Only messages that may require filtering are statuses, since notifications
-      // are already personalized and deletes do not matter
-      if (!needsFiltering || event !== 'update') {
-        transmit(payload);
+      // Streaming only needs to apply filtering to some channels and only to
+      // some events. This is because majority of the filtering happens on the
+      // Ruby on Rails side when producing the event for streaming.
+      //
+      // The only events that require filtering from the streaming server are
+      // `update` and `status.update`, all other events are transmitted to the
+      // client as soon as they're received (pass-through).
+      //
+      // The channels that need filtering are determined in the function
+      // `channelNameToIds` defined below:
+      if (!needsFiltering || (event !== 'update' && event !== 'status.update')) {
+        transmit(event, payload);
         return;
       }
 
-      const targetAccountIds = [payload.account.id].concat(payload.mentions.map(item => item.id));
-      const accountDomain = payload.account.acct.split('@')[1];
+      // The rest of the logic from here on in this function is to handle
+      // filtering of statuses:
 
+      // Filter based on language:
       if (Array.isArray(req.chosenLanguages) && payload.language !== null && req.chosenLanguages.indexOf(payload.language) === -1) {
         log.silly(req.requestId, `Message ${payload.id} filtered by language (${payload.language})`);
         return;
@@ -664,11 +674,16 @@ const startWorker = async (workerId) => {
 
       // When the account is not logged in, it is not necessary to confirm the block or mute
       if (!req.accountId) {
-        transmit(payload);
+        transmit(event, payload);
         return;
       }
 
-      pgPool.connect((err, client, done) => {
+      // Filter based on domain blocks, blocks, mutes, or custom filters:
+      const targetAccountIds = [payload.account.id].concat(payload.mentions.map(item => item.id));
+      const accountDomain = payload.account.acct.split('@')[1];
+
+      // TODO: Move this logic out of the message handling loop
+      pgPool.connect((err, client, releasePgConnection) => {
         if (err) {
           log.error(err);
           return;
@@ -695,28 +710,45 @@ const startWorker = async (workerId) => {
         }
 
         Promise.all(queries).then(values => {
-          done();
+          releasePgConnection();
 
+          // Handling blocks & mutes and domain blocks: If one of those applies,
+          // then we don't transmit the payload of the event to the client
           if (values[0].rows.length > 0 || (accountDomain && values[1].rows.length > 0)) {
             return;
           }
 
-          if (!payload.filtered && !req.cachedFilters) {
+          // If the payload already contains the `filtered` property, it means
+          // that filtering has been applied on the ruby on rails side, as 
+          // such, we don't need to construct or apply the filters in streaming:
+          if (Object.prototype.hasOwnProperty.call(payload, "filtered")) {
+            transmit(event, payload);
+            return;
+          }
+
+          // Handling for constructing the custom filters and caching them on the request
+          // TODO: Move this logic out of the message handling lifecycle
+          if (!req.cachedFilters) {
             const filterRows = values[accountDomain ? 2 : 1].rows;
 
-            req.cachedFilters = filterRows.reduce((cache, row) => {
-              if (cache[row.id]) {
-                cache[row.id].keywords.push([row.keyword, row.whole_word]);
+            req.cachedFilters = filterRows.reduce((cache, filter) => {
+              if (cache[filter.id]) {
+                cache[filter.id].keywords.push([filter.keyword, filter.whole_word]);
               } else {
-                cache[row.id] = {
-                  keywords: [[row.keyword, row.whole_word]],
-                  expires_at: row.expires_at,
-                  repr: {
-                    id: row.id,
-                    title: row.title,
-                    context: row.context,
-                    expires_at: row.expires_at,
-                    filter_action: ['warn', 'hide'][row.filter_action],
+                cache[filter.id] = {
+                  keywords: [[filter.keyword, filter.whole_word]],
+                  expires_at: filter.expires_at,
+                  filter: {
+                    id: filter.id,
+                    title: filter.title,
+                    context: filter.context,
+                    expires_at: filter.expires_at,
+                    // filter.filter_action is the value from the
+                    // custom_filters.action database column, it is an integer
+                    // representing a value in an enum defined by Ruby on Rails:
+                    //
+                    // enum { warn: 0, hide: 1 }
+                    filter_action: ['warn', 'hide'][filter.filter_action],
                   },
                 };
               }
@@ -724,6 +756,10 @@ const startWorker = async (workerId) => {
               return cache;
             }, {});
 
+            // Construct the regular expressions for the custom filters: This
+            // needs to be done in a separate loop as the database returns one
+            // filterRow per keyword, so we need all the keywords before
+            // constructing the regular expression
             Object.keys(req.cachedFilters).forEach((key) => {
               req.cachedFilters[key].regexp = new RegExp(req.cachedFilters[key].keywords.map(([keyword, whole_word]) => {
                 let expr = keyword.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');;
@@ -743,34 +779,56 @@ const startWorker = async (workerId) => {
             });
           }
 
-          // Check filters
-          if (req.cachedFilters && !payload.filtered) {
-            const mutatedPayload = { ...payload };
+          // Apply cachedFilters against the payload, constructing a
+          // `filter_results` array of FilterResult entities
+          if (req.cachedFilters) {
             const status = payload;
-            const searchContent = ([status.spoiler_text || '', status.content].concat((status.poll && status.poll.options) ? status.poll.options.map(option => option.title) : [])).concat(status.media_attachments.map(att => att.description)).join('\n\n').replace(/<br\s*\/?>/g, '\n').replace(/<\/p><p>/g, '\n\n');
-            const searchIndex = JSDOM.fragment(searchContent).textContent;
+            // TODO: Calculate searchableContent in Ruby on Rails:
+            const searchableContent = ([status.spoiler_text || '', status.content].concat((status.poll && status.poll.options) ? status.poll.options.map(option => option.title) : [])).concat(status.media_attachments.map(att => att.description)).join('\n\n').replace(/<br\s*\/?>/g, '\n').replace(/<\/p><p>/g, '\n\n');
+            const searchableTextContent = JSDOM.fragment(searchableContent).textContent;
 
             const now = new Date();
-            mutatedPayload.filtered = [];
-            Object.values(req.cachedFilters).forEach((cachedFilter) => {
-              if ((cachedFilter.expires_at === null || cachedFilter.expires_at > now)) {
-                const keyword_matches = searchIndex.match(cachedFilter.regexp);
-                if (keyword_matches) {
-                  mutatedPayload.filtered.push({
-                    filter: cachedFilter.repr,
-                    keyword_matches,
-                  });
-                }
+            const filter_results = Object.values(req.cachedFilters).reduce((results, cachedFilter) => {
+              // Check the filter hasn't expired before applying:
+              if (cachedFilter.expires_at !== null && cachedFilter.expires_at < now) {
+                return;
               }
-            });
 
-            transmit(mutatedPayload);
+              // Just in-case JSDOM fails to find textContent in searchableContent
+              if (!searchableTextContent) {
+                return;
+              }
+
+              const keyword_matches = searchableTextContent.match(cachedFilter.regexp);
+              if (keyword_matches) {
+                // results is an Array of FilterResult; status_matches is always
+                // null as we only are only applying the keyword-based custom
+                // filters, not the status-based custom filters.
+                // https://docs.joinmastodon.org/entities/FilterResult/
+                results.push({
+                  filter: cachedFilter.filter,
+                  keyword_matches,
+                  status_matches: null
+                });
+              }
+            }, []);
+
+            // Send the payload + the FilterResults as the `filtered` property
+            // to the streaming connection. To reach this code, the `event` must
+            // have been either `update` or `status.update`, meaning the
+            // `payload` is a Status entity, which has a `filtered` property:
+            //
+            // filtered: https://docs.joinmastodon.org/entities/Status/#filtered
+            transmit(event, {
+              ...payload,
+              filtered: filter_results
+            });
           } else {
-            transmit(payload);
+            transmit(event, payload);
           }
         }).catch(err => {
+          releasePgConnection();
           log.error(err);
-          done();
         });
       });
     };