diff --git a/CHANGELOG.md b/CHANGELOG.md
index 253f2f761..8924b03f4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Added
 
 ### Changed
+- **Discord bot**: Improved user onboarding - Activation flow when praising first-time #1070
 
 ### Deprecated
 
diff --git a/packages/api/openapi.json b/packages/api/openapi.json
index ec40bfd91..c5934dc6d 100644
--- a/packages/api/openapi.json
+++ b/packages/api/openapi.json
@@ -1 +1 @@
-{"openapi":"3.0.0","paths":{"/api/activate":{"post":{"operationId":"ActivateController_activate","summary":"Activate a user account in order to be able to give praise and receive rewards. Activation a user account creates a new User object or adds user account to User if it already exists.","parameters":[],"requestBody":{"required":true,"content":{"application/json":{"schema":{"$ref":"#/components/schemas/ActivateInputDto"}}}},"responses":{"200":{"description":"The created (or updated) user.","content":{"application/json":{"schema":{"$ref":"#/components/schemas/User"}}}},"201":{"description":"","content":{"application/json":{"schema":{"$ref":"#/components/schemas/User"}}}}},"tags":["Activate"]}},"/api/users/export/json":{"get":{"operationId":"UsersController_exportJson","summary":"Export users document to json","parameters":[],"responses":{"200":{"description":"","content":{"application/json":{"schema":{"type":"string","format":"binary"}}}}},"tags":["Users"]}},"/api/users/export/csv":{"get":{"operationId":"UsersController_exportCsv","summary":"Export users document to 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The signed message should be structured as follows: \n\n```SIGN THIS MESSAGE TO LOGIN TO PRAISE.\\n\\nADDRESS:\\n[identityEthAddress]\\n\\nNONCE:\\n[nonce]```","content":{"application/json":{"schema":{"$ref":"#/components/schemas/LoginInputDto"}}}},"responses":{"201":{"description":"User authenticated successfully","content":{"application/json":{"schema":{"$ref":"#/components/schemas/LoginResponseDto"}}}}},"tags":["Authentication"]}},"/api/auth/eth-signature/refresh":{"post":{"operationId":"EthSignatureController_token","summary":"Verifies a refreshToken  and returns a JWT token","parameters":[{"name":"host","required":true,"in":"header","schema":{"type":"string"}}],"requestBody":{"required":true,"content":{"application/json":{"schema":{"$ref":"#/components/schemas/GenerateTokenDto"}}}},"responses":{"201":{"description":"Tokens generated 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\ No newline at end of file
diff --git a/packages/discord-bot/src/handlers/activate.ts b/packages/discord-bot/src/handlers/activate.ts
index 8fd36fc23..08f9b8960 100644
--- a/packages/discord-bot/src/handlers/activate.ts
+++ b/packages/discord-bot/src/handlers/activate.ts
@@ -1,8 +1,6 @@
 import { CommandHandler } from '../interfaces/CommandHandler';
-import { getUserAccount } from '../utils/getUserAccount';
-import { GuildMember } from 'discord.js';
-import { getActivateToken } from '../utils/getActivateToken';
 import { renderMessage } from '../utils/renderMessage';
+import { sendActivationMessage } from '../utils/sendActivationMessage';
 
 /**
  * Executes command /activate
@@ -21,45 +19,5 @@ export const activationHandler: CommandHandler = async (
     return;
   }
 
-  try {
-    const userAccount = await getUserAccount(
-      (member as GuildMember).user,
-      host
-    );
-    if (userAccount.user && userAccount.user !== null) {
-      await interaction.editReply({
-        content: await renderMessage(
-          'PRAISE_ACCOUNT_ALREADY_ACTIVATED_ERROR',
-          host
-        ),
-      });
-      return;
-    }
-
-    const activateToken = await getActivateToken(userAccount, host);
-
-    if (!activateToken) {
-      await interaction.editReply({
-        content: 'Unable to activate user account.',
-      });
-      return;
-    }
-
-    const hostUrl =
-      process.env.NODE_ENV === 'development'
-        ? process.env.FRONTEND_URL
-        : `https://${host}`;
-
-    const activationURL = `${hostUrl || 'undefined:/'}/activate?accountId=${
-      member.user.id
-    }&platform=DISCORD&token=${activateToken}`;
-
-    await interaction.editReply({
-      content: `To activate your account, follow this link and sign a message using your Ethereum wallet. [Activate my account!](${activationURL})`,
-    });
-  } catch (error) {
-    await interaction.editReply({
-      content: 'Unable to activate user account.',
-    });
-  }
+  await sendActivationMessage(interaction, host, member);
 };
diff --git a/packages/discord-bot/src/handlers/praise.ts b/packages/discord-bot/src/handlers/praise.ts
index 92f3c179a..69cf75f76 100644
--- a/packages/discord-bot/src/handlers/praise.ts
+++ b/packages/discord-bot/src/handlers/praise.ts
@@ -1,21 +1,15 @@
-import { GuildMember, User } from 'discord.js';
+import { ComponentType, GuildMember } from 'discord.js';
 import { parseReceivers } from '../utils/parseReceivers';
-import { sendReceiverDM } from '../utils/embeds/sendReceiverDM';
-import { renderMessage, ephemeralWarning } from '../utils/renderMessage';
+
+import { ephemeralWarning } from '../utils/renderMessage';
 import { assertPraiseGiver } from '../utils/assertPraiseGiver';
 import { assertPraiseAllowedInChannel } from '../utils/assertPraiseAllowedInChannel';
 import { CommandHandler } from '../interfaces/CommandHandler';
 import { getUserAccount } from '../utils/getUserAccount';
-import { createPraise } from '../utils/createPraise';
-import { praiseSuccessEmbed } from '../utils/embeds/praiseSuccessEmbed';
-import { apiClient } from '../utils/api';
-import {
-  PraisePaginatedResponseDto,
-  UserAccount,
-  Praise,
-} from '../utils/api-schema';
-import { getSetting } from '../utils/settingsUtil';
+
 import { logger } from '../utils/logger';
+import { sendActivationMessage } from '../utils/sendActivationMessage';
+import { givePraise } from '../utils/givePraise';
 
 /**
  * Execute command /praise
@@ -77,160 +71,70 @@ export const praiseHandler: CommandHandler = async (
       return;
     }
 
-    const giverAccount = await getUserAccount(
-      (member as GuildMember).user,
-      host
-    );
+    let giverAccount = await getUserAccount((member as GuildMember).user, host);
 
     if (!giverAccount || !giverAccount.user || giverAccount.user === null) {
-      await ephemeralWarning(
+      const response = await sendActivationMessage(
         interaction,
-        'PRAISE_ACCOUNT_NOT_ACTIVATED_ERROR',
-        host
-      );
-      return;
-    }
-
-    const validReceiverIds: string[] = [
-      ...new Set(
-        parsedReceivers.validReceiverIds.map((id: string) =>
-          id.replace(/\D/g, '')
-        )
-      ),
-    ];
-
-    const selfPraiseAllowed = (await getSetting(
-      'SELF_PRAISE_ALLOWED',
-      host
-    )) as boolean;
-
-    let warnSelfPraise = false;
-    if (
-      !selfPraiseAllowed &&
-      validReceiverIds.includes(giverAccount.accountId)
-    ) {
-      warnSelfPraise = true;
-      validReceiverIds.splice(
-        validReceiverIds.indexOf(giverAccount.accountId),
-        1
-      );
-    }
-
-    const receivers: { guildMember: GuildMember; userAccount: UserAccount }[] =
-      await Promise.all(
-        (
-          await guild.members.fetch({ user: validReceiverIds })
-        ).map(async (guildMember) => {
-          const userAccount = await getUserAccount(guildMember.user, host);
-          return {
-            guildMember,
-            userAccount,
-          };
-        })
+        host,
+        member,
+        true
       );
-
-    let praiseItems: Praise[] = [];
-    if (receivers.length !== 0) {
-      await interaction.editReply({
-        embeds: [
-          await praiseSuccessEmbed(
-            interaction.user,
-            validReceiverIds.map((id) => `<@!${id}>`),
-            reason,
+      if (!response) return;
+
+      try {
+        const collector = response.createMessageComponentCollector({
+          filter: (i) =>
+            i.user.id === interaction.user.id && i.customId === 'retry',
+          componentType: ComponentType.Button,
+          time: 600000,
+        });
+
+        collector.on('collect', async (i) => {
+          giverAccount = await getUserAccount(
+            (member as GuildMember).user,
             host
-          ),
-        ],
-      });
-      praiseItems = await createPraise(
+          );
+
+          if (giverAccount && giverAccount.user) {
+            collector.stop();
+            await givePraise(
+              interaction,
+              guild,
+              member as GuildMember,
+              giverAccount,
+              parsedReceivers,
+              receiverOptions,
+              reason,
+              host,
+              responseUrl
+            );
+            return;
+          }
+
+          await i.update({
+            content:
+              i.message.content +
+              '\nRetry failed... Retry praise after activating on the Praise dashboard',
+          });
+        });
+      } catch {
+        await interaction.editReply(
+          'Timed out... Please use /praise command again.'
+        );
+      }
+    } else {
+      await givePraise(
         interaction,
+        guild,
+        member as GuildMember,
         giverAccount,
-        receivers.map((receiver) => receiver.userAccount),
+        parsedReceivers,
+        receiverOptions,
         reason,
-        host
-      );
-    } else if (warnSelfPraise) {
-      await ephemeralWarning(interaction, 'SELF_PRAISE_WARNING', host);
-    } else if (!receivers.length) {
-      await ephemeralWarning(
-        interaction,
-        'PRAISE_INVALID_RECEIVERS_ERROR',
-        host
-      );
-    } else {
-      await ephemeralWarning(interaction, 'PRAISE_FAILED', host);
-    }
-
-    const hostUrl =
-      process.env.NODE_ENV === 'development'
-        ? process.env?.FRONTEND_URL || 'undefined:/'
-        : `https://${host}`;
-
-    await Promise.all(
-      praiseItems.map(async (praise) => {
-        console.log(praiseItems, receivers);
-        await sendReceiverDM(
-          praise._id,
-          receivers.filter(
-            (receiver) =>
-              receiver.userAccount.accountId === praise.receiver.accountId
-          )[0],
-          member as GuildMember,
-          reason,
-          responseUrl,
-          host,
-          hostUrl,
-          interaction.channelId
-        );
-      })
-    );
-
-    const warningMsgParts: string[] = [];
-
-    if (parsedReceivers.undefinedReceivers) {
-      const warning = await renderMessage(
-        'PRAISE_UNDEFINED_RECEIVERS_WARNING',
         host,
-        {
-          receivers: parsedReceivers.undefinedReceivers.map((id) =>
-            id.replace(/[<>]/, '')
-          ),
-          user: member.user as User,
-        }
+        responseUrl
       );
-      warningMsgParts.push(warning);
-    }
-
-    if (parsedReceivers.roleMentions) {
-      const warning = await renderMessage('PRAISE_TO_ROLE_WARNING', host, {
-        user: member.user as User,
-        receivers: parsedReceivers.roleMentions,
-      });
-      warningMsgParts.push(warning);
-    }
-
-    if (receivers.length !== 0 && warnSelfPraise) {
-      const warning = await renderMessage('SELF_PRAISE_WARNING', host);
-      warningMsgParts.push(warning);
-    }
-
-    const warningMsg = warningMsgParts.join('\n');
-
-    if (warningMsg && warningMsg.length !== 0) {
-      await interaction.followUp({ content: warningMsg, ephemeral: true });
-    }
-
-    const praiseItemsCount = await apiClient
-      .get(`/praise?limit=1&giver=${giverAccount._id}`, {
-        headers: { host },
-      })
-      .then((res) => (res.data as PraisePaginatedResponseDto).totalPages)
-      .catch(() => 0);
-
-    if (receivers.length && receiverOptions.length && praiseItemsCount === 0) {
-      await interaction.followUp({
-        content: await renderMessage('FIRST_TIME_PRAISER', host),
-        ephemeral: true,
-      });
     }
   } catch (err) {
     // eslint-disable-next-line @typescript-eslint/no-explicit-any
diff --git a/packages/discord-bot/src/utils/embeds/praiseEmbeds.ts b/packages/discord-bot/src/utils/embeds/praiseEmbeds.ts
index bcd7ce81b..d178583d5 100644
--- a/packages/discord-bot/src/utils/embeds/praiseEmbeds.ts
+++ b/packages/discord-bot/src/utils/embeds/praiseEmbeds.ts
@@ -1,4 +1,4 @@
-import { User, EmbedBuilder, Role, Embed } from 'discord.js';
+import { User, EmbedBuilder, Role } from 'discord.js';
 import { renderMessage } from '../renderMessage';
 
 export const praiseRoleError = async (
@@ -43,6 +43,6 @@ export const praiseWelcomeEmbed = (
   return new EmbedBuilder()
     .setTitle('Welcome to Praise!')
     .setDescription(
-      `✅ Praise community created\n✅ Praise bot added to Discord\n✅ Praise bot linked to community\n`
+      '✅ Praise community created\n✅ Praise bot added to Discord\n✅ Praise bot linked to community\n'
     );
 };
diff --git a/packages/discord-bot/src/utils/givePraise.ts b/packages/discord-bot/src/utils/givePraise.ts
new file mode 100644
index 000000000..a7c0b5203
--- /dev/null
+++ b/packages/discord-bot/src/utils/givePraise.ts
@@ -0,0 +1,169 @@
+import { getUserAccount } from './getUserAccount';
+import { sendReceiverDM } from '../utils/embeds/sendReceiverDM';
+import { getSetting } from '../utils/settingsUtil';
+import { createPraise } from '../utils/createPraise';
+import { praiseSuccessEmbed } from '../utils/embeds/praiseSuccessEmbed';
+import { apiClient } from '../utils/api';
+import {
+  PraisePaginatedResponseDto,
+  UserAccount,
+  Praise,
+} from '../utils/api-schema';
+import { renderMessage, ephemeralWarning } from './renderMessage';
+import { ParsedReceivers } from './parseReceivers';
+import { ChatInputCommandInteraction, Guild, GuildMember } from 'discord.js';
+
+export const givePraise = async (
+  interaction: ChatInputCommandInteraction,
+  guild: Guild,
+  member: GuildMember,
+  giverAccount: UserAccount,
+  parsedReceivers: ParsedReceivers,
+  receiverOptions: string,
+  reason: string,
+  host: string,
+  responseUrl: string
+): Promise<void> => {
+  if (
+    !parsedReceivers.validReceiverIds ||
+    parsedReceivers.validReceiverIds?.length === 0
+  ) {
+    await ephemeralWarning(interaction, 'PRAISE_INVALID_RECEIVERS_ERROR', host);
+    return;
+  }
+  const validReceiverIds: string[] = [
+    ...new Set(
+      parsedReceivers.validReceiverIds.map((id: string) =>
+        id.replace(/\D/g, '')
+      )
+    ),
+  ];
+
+  const selfPraiseAllowed = (await getSetting(
+    'SELF_PRAISE_ALLOWED',
+    host
+  )) as boolean;
+
+  let warnSelfPraise = false;
+  if (!selfPraiseAllowed && validReceiverIds.includes(giverAccount.accountId)) {
+    warnSelfPraise = true;
+    validReceiverIds.splice(
+      validReceiverIds.indexOf(giverAccount.accountId),
+      1
+    );
+  }
+
+  const receivers: {
+    guildMember: GuildMember;
+    userAccount: UserAccount;
+  }[] = await Promise.all(
+    (
+      await guild.members.fetch({ user: validReceiverIds })
+    ).map(async (guildMember) => {
+      const userAccount = await getUserAccount(guildMember.user, host);
+      return {
+        guildMember,
+        userAccount,
+      };
+    })
+  );
+
+  let praiseItems: Praise[] = [];
+  if (receivers.length !== 0) {
+    await interaction.editReply({
+      content: '',
+      embeds: [
+        await praiseSuccessEmbed(
+          interaction.user,
+          validReceiverIds.map((id) => `<@!${id}>`),
+          reason,
+          host
+        ),
+      ],
+      components: [],
+    });
+
+    praiseItems = await createPraise(
+      interaction,
+      giverAccount,
+      receivers.map((receiver) => receiver.userAccount),
+      reason,
+      host
+    );
+  } else if (warnSelfPraise) {
+    await ephemeralWarning(interaction, 'SELF_PRAISE_WARNING', host);
+  } else if (!receivers.length) {
+    await ephemeralWarning(interaction, 'PRAISE_INVALID_RECEIVERS_ERROR', host);
+  } else {
+    await ephemeralWarning(interaction, 'PRAISE_FAILED', host);
+  }
+
+  const hostUrl =
+    process.env.NODE_ENV === 'development'
+      ? process.env?.FRONTEND_URL || 'undefined:/'
+      : `https://${host}`;
+
+  await Promise.all(
+    praiseItems.map(async (praise) => {
+      console.log(praiseItems, receivers);
+      await sendReceiverDM(
+        praise._id,
+        receivers.filter(
+          (receiver) =>
+            receiver.userAccount.accountId === praise.receiver.accountId
+        )[0],
+        member,
+        reason,
+        responseUrl,
+        host,
+        hostUrl,
+        interaction.channelId
+      );
+    })
+  );
+
+  const warningMsgParts: string[] = [];
+
+  if (parsedReceivers.undefinedReceivers) {
+    const warning = await renderMessage('', host, {
+      receivers: parsedReceivers.undefinedReceivers.map((id) =>
+        id.replace(/[<>]/, '')
+      ),
+      user: member.user,
+    });
+    warningMsgParts.push(warning);
+  }
+
+  if (parsedReceivers.roleMentions) {
+    const warning = await renderMessage('PRAISE_TO_ROLE_WARNING', host, {
+      user: member.user,
+      receivers: parsedReceivers.roleMentions,
+    });
+    warningMsgParts.push(warning);
+  }
+
+  if (receivers.length !== 0 && warnSelfPraise) {
+    const warning = await renderMessage('SELF_PRAISE_WARNING', host);
+    warningMsgParts.push(warning);
+  }
+
+  const warningMsg = warningMsgParts.join('\n');
+
+  if (warningMsg && warningMsg.length !== 0) {
+    await interaction.followUp({ content: warningMsg, ephemeral: true });
+  }
+
+  const praiseItemsCount = await apiClient
+    .get(`/praise?limit=1&giver=${giverAccount._id}`, {
+      headers: { host },
+    })
+    .then((res) => (res.data as PraisePaginatedResponseDto).totalPages)
+    .catch(() => 0);
+
+  if (receivers.length && receiverOptions.length && praiseItemsCount === 0) {
+    await interaction.followUp({
+      content: await renderMessage('FIRST_TIME_PRAISER', host),
+      ephemeral: true,
+    });
+  }
+};
diff --git a/packages/discord-bot/src/utils/parseReceivers.ts b/packages/discord-bot/src/utils/parseReceivers.ts
index 6d23cc918..9a48a7b44 100644
--- a/packages/discord-bot/src/utils/parseReceivers.ts
+++ b/packages/discord-bot/src/utils/parseReceivers.ts
@@ -1,4 +1,4 @@
-interface ParsedReceivers {
+export interface ParsedReceivers {
   validReceiverIds: RegExpMatchArray | null;
   undefinedReceivers: RegExpMatchArray | null;
   roleMentions: RegExpMatchArray | null;
diff --git a/packages/discord-bot/src/utils/renderMessage.ts b/packages/discord-bot/src/utils/renderMessage.ts
index bbe6e31f3..93ff208b7 100644
--- a/packages/discord-bot/src/utils/renderMessage.ts
+++ b/packages/discord-bot/src/utils/renderMessage.ts
@@ -62,6 +62,7 @@ export const ephemeralWarning = async (
   await interaction.deleteReply();
   await interaction.followUp({
     content: await renderMessage(key, host, subs),
+    components: [],
     ephemeral: true,
   });
 };
diff --git a/packages/discord-bot/src/utils/sendActivationMessage.ts b/packages/discord-bot/src/utils/sendActivationMessage.ts
new file mode 100644
index 000000000..02d31e3f3
--- /dev/null
+++ b/packages/discord-bot/src/utils/sendActivationMessage.ts
@@ -0,0 +1,77 @@
+import {
+  ChatInputCommandInteraction,
+  GuildMember,
+  APIInteractionGuildMember,
+  ButtonStyle,
+  ActionRowBuilder,
+  ButtonBuilder,
+  Message,
+} from 'discord.js';
+import { getUserAccount } from '../utils/getUserAccount';
+import { getActivateToken } from '../utils/getActivateToken';
+import { renderMessage } from '../utils/renderMessage';
+
+export const sendActivationMessage = async (
+  interaction: ChatInputCommandInteraction,
+  host: string,
+  member: GuildMember | APIInteractionGuildMember,
+  retry = false
+): Promise<Message | undefined> => {
+  try {
+    const userAccount = await getUserAccount(
+      (member as GuildMember).user,
+      host
+    );
+    if (userAccount.user && userAccount.user !== null) {
+      await interaction.editReply({
+        content: await renderMessage(
+          'PRAISE_ACCOUNT_ALREADY_ACTIVATED_ERROR',
+          host
+        ),
+      });
+      return;
+    }
+
+    const activateToken = await getActivateToken(userAccount, host);
+
+    if (!activateToken) {
+      await interaction.editReply({
+        content: 'Unable to activate user account.',
+      });
+      return;
+    }
+
+    const hostUrl =
+      process.env.NODE_ENV === 'development'
+        ? process.env.FRONTEND_URL
+        : `https://${host}`;
+
+    const activationURL = `${hostUrl || 'undefined:/'}/activate?accountId=${
+      member.user.id
+    }&platform=DISCORD&token=${activateToken}`;
+
+    const activateButton = new ButtonBuilder()
+      .setLabel('Activate')
+      .setURL(activationURL)
+      .setStyle(ButtonStyle.Link);
+    const retryButton = new ButtonBuilder()
+      .setCustomId('retry')
+      .setLabel('Retry')
+      .setStyle(ButtonStyle.Success);
+
+    const row = new ActionRowBuilder<ButtonBuilder>().addComponents(
+      activateButton
+    );
+    if (retry) row.addComponents(retryButton);
+
+    const response = await interaction.editReply({
+      content: `In order to dish praise, you need to activate your account by following this link and signing a message using your Ethereum wallet. [Activate my account!](${activationURL})`,
+      components: [row],
+    });
+    return response;
+  } catch (error) {
+    await interaction.editReply({
+      content: 'Unable to activate user account.',
+    });
+  }
+};