diff --git a/src/analytics/events.ts b/src/analytics/events.ts
index b1f536e..cccd8d3 100644
--- a/src/analytics/events.ts
+++ b/src/analytics/events.ts
@@ -43,10 +43,10 @@ export async function tryToFetchAllCliEvents(): Promise<PosthogEvent[]> {
       retries: 10,
       minTimeout: 5 * 1000,
       maxTimeout: 120 * 1000,
-      onRetry: (e: Error) => {
+      onRetry: (error: Error) => {
+        logger.error(error);
         logger.error(
-          "Error happened while fetching events for report generator, trying again:",
-          e.message ?? e,
+          "Error happened while fetching events for report generator, trying again...",
         );
       },
     },
diff --git a/src/analytics/reports/events.ts b/src/analytics/reports/events.ts
index c14637c..40e9b83 100644
--- a/src/analytics/reports/events.ts
+++ b/src/analytics/reports/events.ts
@@ -12,7 +12,6 @@ import moment from "../moment";
  */
 export async function fetchEventsForReportGenerator(): Promise<PosthogEvent[]> {
   const allEvents = await tryToFetchAllCliEvents();
-
   logger.info("\nNumber of CLI events fetched:", allEvents.length);
 
   const waspTeamFilters = [isNotWaspTeamEvent, isNotMihoPrivateCIServerEvent];
@@ -20,10 +19,17 @@ export async function fetchEventsForReportGenerator(): Promise<PosthogEvent[]> {
     (events, f) => events.filter(f),
     allEvents,
   );
+  logger.debug(
+    "\nNumber of non-Wasp-team CLI events:",
+    nonWaspTeamEvents.length,
+  );
+
   const sortedNonWaspTeamEvents = _.sortBy(nonWaspTeamEvents, "timestamp");
+
   const sortedValidEvents = markAsCiEventBurstsFromDifferentUsersFromSameIp(
     sortedNonWaspTeamEvents,
   );
+  logger.debug("\nNumber of valid CLI events:", sortedValidEvents.length);
 
   return sortedValidEvents;
 }
diff --git a/src/analytics/reports/periodReport/index.ts b/src/analytics/reports/periodReport/index.ts
index 34ae31c..e487a4f 100644
--- a/src/analytics/reports/periodReport/index.ts
+++ b/src/analytics/reports/periodReport/index.ts
@@ -1,3 +1,4 @@
+import logger from "../../../utils/logger";
 import { PosthogEvent } from "../../events";
 import { fetchEventsForReportGenerator } from "../events";
 import { AllTimePeriodReport, PeriodReport } from "../reports";
@@ -14,6 +15,11 @@ export async function generatePeriodReport(
   numPeriods: number,
   periodName: PeriodName,
 ): Promise<PeriodReport> {
+  logger.info("Generating a period report...");
+  logger.debug(
+    `Period report details: numPeriods=${numPeriods}, periodName=${periodName}, prefetchedEvents=${!!prefetchedEvents}`,
+  );
+
   const events = prefetchedEvents ?? (await fetchEventsForReportGenerator());
 
   const userActivityReport = await generateUserActivityReport(
@@ -48,6 +54,11 @@ export async function generateAllTimePeriodReport(
   numPeriods: number,
   periodName: PeriodName,
 ): Promise<AllTimePeriodReport> {
+  logger.info("Generating an all-time period report...");
+  logger.debug(
+    `All-time period report details: numPeriods=${numPeriods}, periodName=${periodName}, prefetchedEvents=${!!prefetchedEvents}`,
+  );
+
   const events = prefetchedEvents ?? (await fetchEventsForReportGenerator());
 
   const userActivityReport = await generateUserActivityReport(
diff --git a/src/analytics/reports/totalReport.ts b/src/analytics/reports/totalReport.ts
index ff98da5..2172323 100644
--- a/src/analytics/reports/totalReport.ts
+++ b/src/analytics/reports/totalReport.ts
@@ -1,3 +1,4 @@
+import logger from "../../utils/logger";
 import { PosthogEvent } from "../events";
 import {
   EventsByExecutionEnvironment,
@@ -16,6 +17,9 @@ import { groupEventsByProject } from "./utils";
 export async function generateTotalReport(
   prefetchedEvents: PosthogEvent[] | undefined = undefined,
 ): Promise<TotalReport> {
+  logger.info("Generating a total report...");
+  logger.debug(`Total report details: prefetchedEvents=${!!prefetchedEvents}`);
+
   const events = prefetchedEvents ?? (await fetchEventsForReportGenerator());
 
   const { localEvents, groupedNonLocalEvents } =
diff --git a/src/discord/bot/analytics/commands.ts b/src/discord/bot/analytics/commands.ts
index 696375c..99e8ae0 100644
--- a/src/discord/bot/analytics/commands.ts
+++ b/src/discord/bot/analytics/commands.ts
@@ -1,5 +1,6 @@
 import Discord from "discord.js";
 
+import logger from "../../../utils/logger";
 import { REPORTS_CHANNEL_ID } from "../../server-ids";
 import { GuildMessage } from "../../types";
 import { fetchTextChannelById } from "../../utils";
@@ -25,6 +26,8 @@ function isReportsChannel(channel: Discord.Channel): boolean {
 export async function handleAnalyticsCommand(
   message: GuildMessage,
 ): Promise<void> {
+  logger.info(`Handling analytics command: ${message.content}...`);
+
   const commandArgs = extractCommandArgs(message.content);
   const analyticsCommand = parseAnalyticsCommand(commandArgs);
   if (!analyticsCommand) {
diff --git a/src/discord/bot/analytics/common.ts b/src/discord/bot/analytics/common.ts
index f39f404..83bb6b2 100644
--- a/src/discord/bot/analytics/common.ts
+++ b/src/discord/bot/analytics/common.ts
@@ -8,6 +8,7 @@ import {
   TextReport,
 } from "../../../analytics/reports/reports";
 import { Writable } from "../../../types/helpers";
+import logger from "../../../utils/logger";
 import { REPORTS_CHANNEL_ID } from "../../server-ids";
 import { fetchTextChannelById } from "../../utils";
 
@@ -19,6 +20,10 @@ export async function sendAnalyticsReportToReportsChannel(
   prefetchedEvents: PosthogEvent[] | undefined = undefined,
   numPeriods: number | undefined = undefined,
 ): Promise<void> {
+  logger.info(`Sending analytics report to the reports channel...`);
+  logger.debug(
+    `Analytics report details: type=${reportType}, numPeriods=${numPeriods}, prefetchedEvents=${!!prefetchedEvents}`,
+  );
   const waspReportsChannel = await fetchTextChannelById(
     discordClient,
     REPORTS_CHANNEL_ID,
@@ -67,11 +72,13 @@ const DISCORD_MESSAGE_TOO_LONG_SUFFIX =
 function convertSimpleReportToDiscordMessage(
   report: Partial<TextReport & ChartReport & ImageChartsReport>,
 ): Discord.MessageCreateOptions {
+  logger.info("Converting report to a Discord message");
   const options: Discord.MessageCreateOptions = {};
   const embeds: Writable<Discord.MessageCreateOptions["embeds"]> = [];
   const files: Writable<Discord.MessageCreateOptions["files"]> = [];
 
   if (report.text) {
+    logger.debug("Report has a `text` field");
     let content: string = report.text.join("\n");
     if (content.length >= DISCORD_MAX_MSG_SIZE) {
       content =
@@ -84,12 +91,16 @@ function convertSimpleReportToDiscordMessage(
   }
 
   if (report.imageChartsChart) {
+    logger.debug(
+      `Report has a \`imageChartsChart\` field (URL=${report.imageChartsChart.toURL()})`,
+    );
     embeds.push(
       new Discord.EmbedBuilder().setImage(report.imageChartsChart.toURL()),
     );
   }
 
   if (report.bufferChart) {
+    logger.debug("Report has a `bufferChart` field");
     files.push(report.bufferChart);
   }
 
diff --git a/src/discord/bot/daily-standup.ts b/src/discord/bot/daily-standup.ts
index bed0b0d..e931758 100644
--- a/src/discord/bot/daily-standup.ts
+++ b/src/discord/bot/daily-standup.ts
@@ -2,12 +2,14 @@ import Discord from "discord.js";
 import InspirationalQuotes from "inspirational-quotes";
 import _ from "lodash";
 
+import logger from "../../utils/logger";
 import { DAILY_STANDUP_CHANNEL_ID } from "../server-ids";
 import { fetchTextChannelById } from "../utils";
 
 export async function initiateDailyStandup(
   discordClient: Discord.Client,
 ): Promise<void> {
+  logger.info(`Initiating daily standup...`);
   const dailyStandupChannel = await fetchTextChannelById(
     discordClient,
     DAILY_STANDUP_CHANNEL_ID,
diff --git a/src/discord/bot/introduction.ts b/src/discord/bot/introduction.ts
index 497472d..675902a 100644
--- a/src/discord/bot/introduction.ts
+++ b/src/discord/bot/introduction.ts
@@ -24,8 +24,11 @@ async function isGuestUser(message: GuildMessage): Promise<boolean> {
 export async function handleIntroductionMessage(
   message: GuildMessage,
 ): Promise<void> {
+  logger.info(`Handling introduction message [${message.id}]...`);
+
   const trimmedMessageLength = message.content.trim().length;
   if (trimmedMessageLength < 20) {
+    logger.debug(`Introduction message [${message.id}] is too short`);
     await message.reply(
       "👋 Great to have you here! Please introduce yourself with a message that's at least 2️⃣0️⃣ characters long and I will give you full access to the server.",
     );
@@ -33,6 +36,9 @@ export async function handleIntroductionMessage(
   }
 
   try {
+    logger.debug(
+      `Introduction message [${message.id}] is valid. Removing the guest role...`,
+    );
     const member = await message.guild.members.fetch(message.author.id);
     await member.roles.remove(GUEST_ROLE_ID);
     await message.reply(