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December 17, 2025
Enhanced Personalization in Sidekick Voice
Sidekick Voice now greets returning Customers by name when their phone number matches an existing Customer Profile. This simple touch creates a more welcoming and personalized interaction from the first hello.
Dynamic Variables in Answer Links
Your Answers now support dynamic variables within links, automatically replacing placeholders with real values when Agents use them. This means links stay accurate and personalized without manual updates. Use the '/var' button in the link editor to set it up.
More Complete Reporting in Sidekick Dashboards
The Sidekick Dashboard now shows the full picture of your conversations, including those that have been reopened or managed outside the platform after handoff. Get a clearer view of resolutions and where Conversations actually land.
90-Day Data Retention for Sidekick Conversations
Sidekick Conversation data is now retained for up to 90 days. This ensures managers can quickly and efficiently monitor Sidekick interactions in real-time without losing visibility into recent activity from the Sidekick Conversations page.
Gladly Support Holiday Hours
Gladly Support will operate with slightly reduced staffing due to the Christmas and New Year holidays.
P1 and P2 requests will be handled as usual, with a 24/7 on-call team available throughout the holidays. Please ensure your request meets the priority level business impact requirements.
Response times will remain unchanged, except for December 24th–25th and January 1st, when P3 and P4 requests may experience a delay.
For your reference, and in the event of an unexpected platform issue, we recommend you bookmark our incident response guide to understand the necessary action items.
No Release Update Weeks of December 22 and December 29
Please be advised that there will be no release update or email during the weeks of December 22 and December 29 in observance of Christmas and New Years.
[Action Required] Update IVR Holiday Schedule
Update your Gladly IVR to confirm the Schedule node (typically named "Holiday Check") displays the correct year. This ensures your IVR routes calls correctly during your holiday hours. Watch this quick overview video to learn how.
[Coming Soon] Automatic Topic Assignment for Sidekick Guides
In January, Sidekick will automatically apply your key contact reasons as Topics for conversations where Topics haven't been manually assigned - keeping your AI conversations categorized the same way your agents handle them.
You can also manually apply Topics directly within a Guide to trigger automation workflows like intelligent routing to specific Inboxes. Learn more about best practices for using Topics in Guides.
Learn more about best practices and key use cases for applying Topics within a Guide.
A Better Answer Guide Experience is on the Way
Over the next few weeks, we’ll be upgrading your Sidekick Answers Guide to the new and improved Questions and Recommendations Guide. This enhanced Guide offers the same functionality you’re familiar with—just smarter and more impactful.
With this new Guide, you can point Sidekick to specific websites, letting it pull information directly from your trusted sources. This means Sidekick can answer a broader range of customer questions and deliver more precise recommendations. Learn how to configure websites here. No action is needed on your end, and there’s no loss of functionality—only a smoother experience designed to help Sidekick deliver even better responses.
No action needed on your end—there's no loss of functionality, and your previous Answers Guide will remain available under the 'Inactive' tab for reference.
Do Not Set SMS Preference During Mobile Number Lookup
Fixed – Updated mobile phone number lookup logic so that the SMS preference is not automatically set to ‘On’ when creating a Customer Profile.
Login Form Submits Twice
Fixed – Prevented Agents from submitting the login form twice, which previously could result in them being logged out.
Keep Assignee During Conversation Merge if Source is Automation
Fixed – When merging a Conversation from the Automation Inbox, the assignee of the merged Conversation now stays the same. For Conversations from other Inboxes, the assignee continues to update to match the source Conversation.
RESOURCE
Sidekick Returns & WISMR Guides: From Setup to Success
Master two of your highest-impact Sidekick workflows with this on-demand classroom. Learn how to build, customize, test, and optimize Returns and Where Is My Return guides—plus track performance in Journeys to improve resolution rates and customer confidence.
RESOURCE
Stop Buying Voice AI Like Software—Evaluate It Like a Team Member
Voice AI isn’t just another tool—it’s a key member of your CX team. Learn how to assess business fit, technical skill, and readiness to ensure your AI delivers real impact and seamless customer experiences.
RESOURCE
The Hidden Economics of Cheap AI
AI can cut costs—or erode trust. This article breaks down why many AI deployments fail and how to shift from chasing quick wins to creating measurable customer value. Learn how to use AI strategically, protect your brand, and deliver CX that’s both radically efficient and personal.
EVENT
Get an Early Look at Your 2026 CX Playbook
A new wave of tools, expectations, and opportunities is shaping the year ahead. At Gladly Connect Live 2026 this May in Atlanta, experts will break down the trends that matter most and how to turn them into more efficient, more personal customer experiences. You’ll walk away with a clear view of where CX is heading and how to stay one step ahead.
REVIEWS
You're In Good Company
Love using Gladly? Share your experience on G2 Crowd to help others discover how Gladly empowers better customer connections.
REVIEWS
Using Gladly with your Shopify store?
Using Gladly with your Shopify store? We'd love your feedback there too! Leave us a review on the Shopify App Store and help other merchants discover how Gladly creates seamless, revenue-driving conversations.
RESOURCE
Gladly Referral Promotion
Love using Gladly? Now’s your chance to share the experience with others in your professional network. Submit your B2C or e-commerce referral to receive up to $2,000! Visit the Refer-A-Friend program to learn how.
December 10, 2025
Abandoned Chat Detection
Abandoned chats waste Agent capacity without driving any value. With Gladly's new Abandoned Chat feature, your team can automatically detect and close Abandoned Chats, freeing your team to handle the Conversations that actually matter.
What's new:
Automatic detection and closure: Gladly now identifies when a Customer abandons a Chat and closes the Contact automatically, opening up a new concurrency slot for the Agent.
If the Customer abandons before the Chat is routed, the Conversation is closed automatically.
If the Customer abandons mid-Conversation, after the Chat has been routed to an Agent and an Inbox, the Conversation moves to Waiting, allowing the Agent to assist a new Customer and return to close the abandoned Conversation when the queue slows down.
Configurable settings: Admins can turn the Abandoned Chat feature on and off from Gladly Settings and set the timeout window to match how your team works.
New reporting field: A 'Customer Abandoned Contact' column has been added to the Contact Export report—a simple yes/no field that shows whether a Customer abandoned the Conversation. This applies to all Channels where abandonment is tracked: Phone Calls and Chat.
Why it matters:
Reclaim Agent capacity that's currently tied up in dead Conversations.
Reduce Customer wait times and maintain service levels during peak volume.
Gain clear visibility into Conversation lifecycle without touching dashboards.
Delivers on the most frequently requested operational efficiency feature.
New Field in Conversation Export with Sidekick Report
We've added the "Sidekick Channel Name" field to the Conversation Export with Sidekick report, giving you complete visibility into how Conversations flow across your Sidekick Channels—including Custom Channels. Now you can track performance and channel usage in a single, unified view.
Easier Revenue Tracking for Sidekick
It’s now simpler to measure Sidekick’s revenue impact. Connect your Google Analytics in one step and see exactly how Sidekick-assisted and Agent-assisted Conversations influence purchases—no developer work required.
What’s new:
One-step setup: Add your Google Analytics ID and you’re done.
Automatic attribution: Every Chat is linked to purchases, even if Customers buy later.
Clear visibility: New attribution reports let you see revenue impact by Guide, Agent type, or time range.
Why it matters:
See exactly how much revenue Sidekick influences so you can make data-driven decisions about scaling it. Compare Sidekick-driven vs. Agent-driven revenue to understand the real impact.
Sidekick Assists by Classification Topic Report Sunset
The Sidekick Assists by Classification Topic report has been deprecated in favor of newer Sidekick out-of-the-box reports and dashboards that better reflect current definitions and metrics.
We recommend using reports listed below instead:
Conversation Export—enhanced with seven Sidekick fields for deeper insight
[Coming Soon] Automatic Topic Assignment for Sidekick Guides
In January, Sidekick will automatically apply your key contact reasons as Topics for Conversations where Topics haven't been manually assigned. This keeps your AI conversations consistent with how your Agents handle them.
As a reminder, you can now manually apply existing Topics directly within a Guide. This allows teams to gain visibility into Customer contact reasons and trigger automation workflows—like routing to an Inbox—for Conversations handled by Sidekick.
Learn more about best practices and key use cases for applying Topics within a Guide.
[Action Required] Update IVR Holiday Schedule
It’s time to review your Gladly IVR for the holidays.
Please confirm that your Schedule node (typically named “Holiday Check”) is using the correct year and dates so your IVR routes calls properly during holiday hours.
Watch this quick overview video to see how to verify and update your IVR holiday settings.
A Better Answer Guide Experience is on the Way
Over the next few weeks, we’ll be upgrading your Sidekick Answers Guide to the new and improved Questions and Recommendations Guide. This enhanced Guide offers the same functionality you’re familiar with—just smarter and more impactful.
With this new Guide, you can point Sidekick to specific websites, letting it pull information directly from your trusted sources. This means Sidekick can answer a broader range of customer questions and deliver more precise recommendations. Learn how to configure websites here. No action is needed on your end, and there’s no loss of functionality—only a smoother experience designed to help Sidekick deliver even better responses.
Note: Your previous Answers Guide will remain available under the ‘Inactive’ tab within Sidekick Guides for reference.
No Release Update Weeks of December 22 and December 29
Please be advised that there will be no release update or email during the weeks of December 22 and December 29 in observance of Christmas and New Years.
Gladly Support Holiday Hours
Gladly Support will have reduced staffing from Wednesday, December 24 through Thursday, January 2 for the Christmas and New Year holidays.
For steps to follow during an unexpected platform issue, review our incident response guide.
Deleted Company Numbers No Longer Displayed
Fixed – Company phone numbers that have been removed from your organization will no longer appear under ‘Existing Numbers’ when setting up a new SMS or Voice number.
RESOURCE
Sidekick Reporting: Unlock Workflows and Insights to Drive Results
Level up your Sidekick reporting skills with our new on-demand classroom. Learn how to read key dashboards, identify performance trends, and turn insights into actionable improvements
RESOURCE
How PACT Proves AI ROI (And Gets CFO Buy-In)
In this new podcast episode, PACT’s Lauren Inman-Semerau shares the exact framework she uses to evaluate AI tools, avoid “AI sparkle,” and model ROI over 3, 6, and 12 months. If you're working on your AI business case or sharpening your strategy, this is must-watch guidance from a peer who's doing it in real time.
RESOURCE
The AI Savings That Cost You Millions
Not all AI “wins” are really wins. In this new piece, we break down why deflection-first automation can quietly erode loyalty—and how brands are shifting toward AI that protects lifetime value instead of sacrificing
EVENT
Make CX More Human With AI
Behind every great customer experience is a great team. At Gladly Connect Live 2026 in Atlanta this May, you’ll see how companies are using AI to support their agents by removing busywork, giving them better context, and creating space for the human moments that matter. The technology is powerful, but its real value is how it helps people shine.
REVIEWS
You're In Good Company
Love using Gladly? Share your experience on G2 Crowd to help others discover how Gladly empowers better customer connections.
REVIEWS
Using Gladly with your Shopify store?
Using Gladly with your Shopify store? We'd love your feedback there too! Leave us a review on the Shopify App Store and help other merchants discover how Gladly creates seamless, revenue-driving conversations.
RESOURCE
Gladly Referral Promotion
Love using Gladly? Now’s your chance to share the experience with others in your professional network. Submit your B2C or e-commerce referral to receive up to $2,000! Visit the Refer-A-Friend program to learn how.
December 3, 2025
Clearer Estimated Wait Time Display and Smarter Rule Handling
Customers now see easier-to-read wait times in auto-reply messages. Instead of "5h27m," Customers will see "5 hours 27 minutes."
We've also improved how the Estimated Remaining Wait Time rule condition handles scenarios where no Agents are working, ensuring more accurate rule behavior.
For examples of how to use Estimated Wait Time in your automations, visit the Common Rules Library.
Topics Now Reflected Across Sidekick Reporting
Topics applied to Sidekick Conversations now appear in the Topics Dashboard, Sidekick Dashboard, and Conversation Export—even for Conversations not handled by an Agent. This gives you more complete visibility into Topic data across all Conversations.
[Coming Soon] Automatic Topic Assignment for Sidekick Guides
Starting in December, Sidekick will automatically apply Topics to Conversations where you haven't manually assigned them within a Guide. This ensures consistency between automated and Hero-led Conversations.
As a reminder, you can now manually apply existing Topics directly within a Guide. This allows teams to gain visibility into Customer contact reasons and trigger automation workflows—like routing to an Inbox—for Conversations handled by Sidekick.
Learn more about best practices and key use cases for applying Topics within a Guide.
[Action Required] Update IVR Holiday Schedule
It’s time to review your Gladly IVR for the holidays.
Please confirm that your Schedule node (typically named “Holiday Check”) is using the correct year and dates so your IVR routes calls properly during holiday hours.
Watch this quick overview video to see how to verify and update your IVR holiday settings.
A Better Answer Guide Experience is on the Way
Sidekick’s getting smarter. Over the next few weeks, your current Answers Guide will evolve into the new Questions and Recommendations Guide–same foundation, just more impactful and precise.
You’ll soon be able to point Sidekick to trusted websites so it can pull up-to-date information about your products, company policies, store hours, locations, and other key details, all straight from your brand’s own sources.
No setup needed, no downtime—just a smoother experience built for better answers.
Note: Your previous Answers Guide will remain available under the ‘Inactive’ tab within Sidekick Guides for reference.
Sidekick Assists by Classification Topic Report Moved to Sunsetting
The Sidekick Assist by Classification Topic report has been moved to the Sunsetting category. While it will remain available until December 8, 2025, it’s being phased out in favor of newer Sidekick out-of-the-box reports and dashboards that better reflect current definitions and metrics.
To prepare, we recommend using reports listed below instead:
Conversation Export — now enhanced with six new Sidekick fields for deeper insight
No Release Update Week of December 22 and December 29
Please be advised that there will be no release update or email during the weeks of December 22 and December 29 in observance of Christmas and New Years.
Gladly Support Holiday Hours
Gladly Support will have reduced staffing from Wednesday, December 24 through Thursday, January 2 for the Christmas and New Year holidays.
For steps to follow during an unexpected platform issue, review our incident response guide.
Sidekick Answer Data Now Visible in Journeys
Fixed – Answers referenced by Sidekick within a Questions & Recommendations Guide now appear correctly in Answer Performance and Suggested Answers sections of Journeys, ensuring complete performance data.
RESOURCE
New On-Demand Learning Library
We’ve launched an on-demand learning library to help you get the most out of Sidekick. Access in-depth walkthroughs for setting up and fine-tuning key Guide use cases and Sidekick configurations—anytime, at your own pace.
RESOURCE
Final Checks Before the Holidays
If you missed our Holiday Preparedness Classroom Session, the on-demand replay covers the key best practices, configuration checks, and Sidekick adjustments that keep service running smoothly through the holidays.
You can also review the Holiday Preparation Checklist for a quick rundown of the settings, content updates, and operating-hour changes keep things running smoothly. Together, these resources will help your team stay confident and prepared through the busiest weeks of the year.
EVENT
See What Actually Works With AI
Plenty of teams are experimenting with AI, but only a few are seeing meaningful results. At Gladly Connect Live 2026 this May in Atlanta, brands will openly share what they’ve learned: the choices that delivered impact, the ones they’d rethink, and the plays they rely on today. It’s a chance to get beyond the hype and focus on what truly drives performance.
REVIEWS
You're In Good Company
Love using Gladly? Share your experience on G2 Crowd to help others discover how Gladly empowers better customer connections.
REVIEWS
Using Gladly with your Shopify store?
Using Gladly with your Shopify store? We'd love your feedback there too! Leave us a review on the Shopify App Store and help other merchants discover how Gladly creates seamless, revenue-driving conversations.
RESOURCE
Gladly Referral Promotion
Love using Gladly? Now’s your chance to share the experience with others in your professional network. Submit your B2C or e-commerce referral to receive up to $2,000! Visit the Refer-A-Friend program to learn how.