PDF Security & Access Issues

How to Fix the Please Try Again Error When Sending PDFs for Signature

Ayan MasoodAyan Masood Nov 3, 2026 870 views

Question details

Users encounter a continuous 'Please try again' error message when attempting to send a PDF document for an electronic signature, frequently occurring after updating the account email address.

How to Fix the 'Please Try Again' Error When Sending PDFs for Signature
Product
Adobe Acrobat / Adobe Sign
Device & OS
not provided
Scenario
Requesting an electronic signature for a PDF document via a built-in cloud service.
Observed behavior
The signature request process halts and displays a 'Please try again' prompt, preventing the user from successfully sending the document to the intended recipients.
Before you start

Verify that your internet connection is stable and ensure you know the exact email address currently linked to your active, paid PDF software subscription.

Solution 1Recommended

Re-authenticate with the Correct Subscription Account

Signing out and signing back in refreshes your account entitlements, which often resolves errors caused by logging in with a free account or an unverified email.

Many users accidentally log in using a secondary email address that does not have an active Adobe Acrobat or Adobe Sign subscription. Free accounts typically have strict usage limits (such as two signature requests per month) which can trigger generic error messages once exceeded.

1
Sign out of the application

Open your PDF software, click on your profile icon in the top right corner or navigate to the 'Help' menu, and select 'Sign Out'.

2
Verify your email address

Check your email inbox for any pending account verification links from the software provider and click the link to confirm your email is active.

3
Sign back in with the paid account

Relaunch the application and log in using the exact Adobe ID or email address that is officially associated with your paid subscription.

Free Account Limitations: If you are using the free Acrobat Reader DC, you are limited to sending only two documents for signature per month on a rolling basis.

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Bypass complex account synchronization errors and monthly limits by using WPS Office to securely sign and manage your PDF documents directly on your device.

  1. 1. Open your PDF in WPS: Launch WPS Office and open the PDF document you need to sign.
  2. 2. Access the Fill & Sign tool: Navigate to the 'Protect' or 'Edit' tab on the top ribbon and click on the 'PDF Signature' or 'Fill & Sign' option.
  3. 3. Apply your signature: Create a new signature by typing, drawing, or uploading an image, then place it anywhere on the document.
  4. 4. Save and share: Save the signed PDF locally or share it directly with your recipients via email from within the application.
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Frequently Asked Questions

Why do I get a limit reached message when sending a PDF for signature?

Free PDF accounts, such as Adobe Acrobat Reader DC, limit users to sending only two documents for signature per month. Once this limit is reached, you will encounter errors unless you upgrade to a premium subscription or wait for the rolling month to reset.

Does changing my account email address affect my PDF subscription?

Yes, it can. If you change the email address associated with your account, the software's backend may fail to sync your paid entitlements to the new email immediately, leading to authentication and 'Please try again' errors when using premium features.

How can I verify which email is linked to my paid PDF subscription?

Log into your account portal on the provider's official website (e.g., the Adobe Account management page) and navigate to the 'Plans' or 'Subscriptions' section to confirm which email address holds the active billing agreement.