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Email Delivery Issues

Quick Reference​

Having trouble with emails not sending or going to spam? This guide covers common email delivery problems in ShootPath, from Gmail integration issues to SMTP connection errors.

Common Email Problems:

  • Emails not sending → Check email integration connection
  • Emails going to spam → Improve sender reputation, use proper formatting
  • SMTP connection errors → Verify SMTP settings and credentials
  • Gmail integration not working → Reauthorize OAuth connection
  • Client not receiving emails → Ask client to check spam, whitelist your address

Quick Troubleshooting:

  1. Check email integration: Settings → Integrations → Email (should show "Connected")
  2. Check sent email logs: Settings → Integrations → Email → Recent Emails
  3. Send test email to yourself
  4. Check spam folder
  5. Verify client email address is correct
Most Common Causes

95% of email issues are caused by:

  1. Email integration not connected (check Settings → Integrations)
  2. Gmail security settings blocking the connection (enable "Less secure app access")
  3. Emails going to client's spam folder (ask them to check)

Detailed Guide​

Emails Not Sending​

If you're trying to send an email and it's not going out:

Step 1: Check Email Integration Status

  1. Go to Settings → Integrations
  2. Find the Email section
  3. Check status:
    • Connected (green checkmark) - Integration is working
    • Not Connected or Disconnected (red X) - Integration needs setup/reconnection

If Not Connected: You must connect an email service before you can send emails. See Connecting Email Integration below.

Step 2: Check Recent Email Logs

  1. Go to Settings → Integrations → Email
  2. Scroll down to Recent Emails Sent
  3. Find the email you tried to send
  4. Check status:
    • Sent: Successfully delivered to mail server
    • Delivered: Confirmed received by recipient
    • Bounced: Email address doesn't exist or mailbox full
    • Failed: Error occurred (click for details)
    • Not Found: Email was never sent (check if you clicked "Send")

If Status is "Failed":

  • Click the email to see error message
  • Common errors and solutions below

Step 3: Common Error Messages

Error: "Email integration not configured"

  • Solution: Connect Gmail or SMTP in Settings → Integrations → Email

Error: "Daily sending limit exceeded"

  • Gmail free accounts: 500 emails/day
  • Gmail Workspace accounts: 2,000 emails/day
  • SMTP providers: Varies by provider
  • Solution: Wait 24 hours for limit to reset, or upgrade email service

Error: "Authentication failed"

  • Gmail: OAuth connection expired, reconnect in Settings
  • SMTP: Username/password incorrect, update in Settings
  • Solution: Reconnect email integration

Error: "Recipient address rejected"

  • Client email address is invalid
  • Common issues: typos, spaces, missing @, wrong domain
  • Solution: Fix client's email address in ShootPath and resend

Error: "Connection timeout"

  • Email server is temporarily unreachable
  • Could be your internet, Gmail's servers, or SMTP server
  • Solution: Wait 10 minutes and try again

Error: "Relay access denied"

  • SMTP server requires authentication
  • Or: SMTP server doesn't allow relaying from your IP
  • Solution: Check SMTP settings, ensure username/password are correct

Error: "Attachment too large"

  • Most email services limit attachments to 25MB
  • ShootPath attachments rarely exceed this (PDFs are small)
  • If you're attaching photos: Use gallery links instead

Step 4: Send a Test Email

Send an email to yourself to test the integration:

  1. Create a test job with your own email as the client
  2. Send a quote or invoice email
  3. Check if you receive it

If you receive it:

  • Email integration works correctly
  • The problem is specific to certain clients (see Emails Going to Spam)

If you don't receive it:

  • Check your spam folder
  • Check email logs for errors
  • Email integration has a problem (see below)

Connecting Email Integration​

ShootPath supports two email methods:

Option 1: Gmail (Recommended for Most Users)

  • Easy setup (one-click OAuth)
  • Reliable delivery
  • Free for up to 500 emails/day
  • Works with personal Gmail or Google Workspace

Option 2: SMTP (For Advanced Users)

  • Works with any email provider (SendGrid, Mailgun, Amazon SES, etc.)
  • Requires technical setup
  • Better for high-volume sending (1000+ emails/day)
  • Better deliverability for custom domains

Connecting Gmail:

Step 1: Start Connection

  1. Go to Settings → Integrations
  2. Find Email section
  3. Click Connect Gmail

Step 2: Choose Google Account

  • You'll be redirected to Google sign-in
  • Choose the Gmail account you want to use for sending emails
  • This should be your business email (e.g., your-email@example.com)

Step 3: Authorize ShootPath

  • Google will show: "ShootPath wants to access your Gmail account"
  • Permissions requested:
    • Send emails on your behalf
    • View email address
  • Click Allow

Step 4: Confirm Connection

  • You'll be redirected back to ShootPath
  • You'll see: "Gmail connected successfully"
  • Email section should now show: Connected (green checkmark)

Step 5: Test the Connection

  • Send a test email to yourself
  • Check if you receive it

If Authorization Fails:

Error: "Access blocked: This app's request is invalid"

  • Google Workspace admins can block third-party apps
  • Solution: Ask your IT admin to whitelist ShootPath in Google Workspace admin console
  • Or: Use a personal Gmail account instead

Error: "This app isn't verified"

  • Google showing a security warning
  • Click Advanced → Go to ShootPath (unsafe) (it's safe, we're just not fully verified yet)
  • Or: Use SMTP instead

Connecting SMTP:

You'll need these details from your email provider:

Required Information:

  • SMTP Host: e.g., smtp.gmail.com, smtp.sendgrid.net
  • SMTP Port: Usually 587 (TLS) or 465 (SSL)
  • Username: Your email address or account username
  • Password: Your email password or app-specific password
  • Encryption: TLS or SSL

Common SMTP Settings:

Gmail:

  • Host: smtp.gmail.com
  • Port: 587
  • Encryption: TLS
  • Username: your-email@gmail.com
  • Password: App-specific password (not your regular Gmail password)

Google Workspace:

SendGrid:

  • Host: smtp.sendgrid.net
  • Port: 587
  • Encryption: TLS
  • Username: apikey
  • Password: Your SendGrid API key

Mailgun:

  • Host: smtp.mailgun.org
  • Port: 587
  • Encryption: TLS
  • Username: Your Mailgun SMTP username
  • Password: Your Mailgun SMTP password

Setup Steps:

  1. Go to Settings → Integrations → Email
  2. Click Configure SMTP
  3. Enter all required fields
  4. Click Test Connection
  5. If test succeeds, click Save

If Test Fails:

Error: "Could not connect to SMTP server"

  • Check host and port are correct
  • Check your firewall isn't blocking port 587 or 465
  • Try alternate port (587 vs 465)

Error: "Authentication failed"

  • Username or password is wrong
  • For Gmail: You need an app-specific password, not your regular password (see Gmail SMTP Setup)

Error: "SSL/TLS error"

  • Wrong encryption setting
  • Try TLS instead of SSL, or vice versa

Gmail Integration Issues​

If Gmail was connected but stopped working:

Reconnect Gmail:

  1. Go to Settings → Integrations
  2. Find Email section
  3. Click Disconnect
  4. Click Connect Gmail
  5. Authorize again

Common Gmail Problems:

Problem: "Less secure app access" Error

Gmail may block ShootPath if "Less secure app access" is disabled.

For Personal Gmail Accounts:

  1. Go to myaccount.google.com/lesssecureapps
  2. Turn ON "Allow less secure apps"
  3. Return to ShootPath and reconnect Gmail

For Google Workspace Accounts:

  1. This setting is controlled by your IT admin
  2. Ask admin to enable "Less secure apps" for your account
  3. Or: Use SMTP with app-specific password instead

Problem: "Account Access Disabled" Email from Google

Google may send you an email: "Someone just tried to sign in to your Google Account"

Solution:

  1. In the email, click Yes, it was me
  2. This tells Google ShootPath is authorized
  3. Return to ShootPath and try connecting again

Problem: Two-Factor Authentication Enabled

If you have 2FA on your Gmail:

  • OAuth connection (Connect Gmail button) should still work
  • If using SMTP: You must create an app-specific password

Creating App-Specific Password:

  1. Go to myaccount.google.com/apppasswords
  2. Click Select app → Other (custom name)
  3. Enter "ShootPath"
  4. Click Generate
  5. Google shows a 16-character password
  6. Copy this password
  7. In ShootPath SMTP settings, paste this as your password (not your regular Gmail password)

Emails Going to Spam​

If emails are sending successfully but clients say they never received them:

Step 1: Verify Email Was Sent

  1. Go to Settings → Integrations → Email → Recent Emails
  2. Find the email
  3. Check status is "Sent" or "Delivered"

If status is "Delivered," the email definitely reached the client's mail server. It's either in their inbox or spam.

Step 2: Ask Client to Check Spam

Most email providers have spam filters that can incorrectly flag legitimate emails.

Gmail:

  • Check Spam folder
  • Check Promotions tab
  • Check Updates tab

Outlook/Hotmail:

  • Check Junk Email folder
  • Check Focused vs Other tabs

Yahoo:

  • Check Spam folder
  • Check Bulk folder

Corporate Email (Office 365, etc.):

  • Check Junk Email folder
  • Check with IT if emails are quarantined

If Found in Spam: Have client:

  1. Mark the email as "Not Spam" or "Not Junk"
  2. Add your email address to their contacts
  3. Create a filter to always move your emails to inbox

Step 3: Improve Email Deliverability

Why Emails Go to Spam:

  • Sending domain has poor reputation
  • Email content looks like spam (too many links, ALL CAPS, etc.)
  • No SPF/DKIM records (technical email authentication)
  • Client's email provider is overly aggressive

How to Avoid Spam:

Use a Professional Email Domain:

Improve Email Content:

  • Avoid ALL CAPS in subject lines
  • Don't use spam trigger words (FREE, URGENT, ACT NOW, LIMITED TIME)
  • Keep links minimal (ShootPath emails only include necessary links)
  • Personalize with client's name
  • Write naturally, not like marketing copy

Set Up Email Authentication (Advanced): If you're using SMTP with a custom domain, configure:

  • SPF record: Tells receiving servers your SMTP server is authorized
  • DKIM record: Cryptographically signs your emails
  • DMARC record: Tells receivers how to handle failed authentication

These are DNS records. Ask your domain registrar or IT admin for help setting them up.

Send Test Emails: Use mail-tester.com:

  1. Send an email from ShootPath to the address mail-tester provides
  2. Check your score (out of 10)
  3. Fix issues identified (missing SPF/DKIM, spam content, etc.)

Warm Up Your Sending Domain: If you just started using a new email address:

  • Send a few emails per day for the first week
  • Gradually increase volume
  • This builds sender reputation with email providers

Step 4: Have Client Whitelist Your Address

Provide these instructions to clients:

Gmail:

  1. Open an email from you
  2. Click the three dots → Add [your-name] to Contacts
  3. Or: Settings → Filters → Create new filter → From: [your-email] → Never send to Spam

Outlook:

  1. Open an email from you
  2. Right-click on sender → Add to Contacts
  3. Or: Settings → Junk email → Safe senders → Add [your-email]

Yahoo:

  1. Open an email from you
  2. Click Add to Contacts
  3. Or: Settings → Filters → Add new filter → From contains [your-email] → Move to Inbox

SMTP Connection Errors​

If you're using SMTP and getting connection errors:

Error: "Could not connect to SMTP host"

Possible Causes:

  • SMTP host is wrong (typo, missing smtp. prefix)
  • SMTP port is wrong (try 587 or 465)
  • Your firewall is blocking the port
  • SMTP server is temporarily down

Solutions:

  1. Double-check host and port with your email provider's documentation
  2. Try port 587 (TLS) instead of 465 (SSL), or vice versa
  3. Check if your router/firewall blocks outbound port 587/465
  4. Contact your email provider to confirm SMTP details

Error: "Authentication failed"

Possible Causes:

  • Username is wrong (should be full email address for most providers)
  • Password is wrong
  • For Gmail with 2FA: Need app-specific password, not regular password

Solutions:

  1. Verify username is correct (usually your full email address)
  2. Verify password is correct
  3. For Gmail: Create app-specific password (see Gmail SMTP Setup)
  4. For other providers: Confirm password hasn't expired or been reset

Error: "Relay access denied"

Possible Causes:

  • SMTP server doesn't allow relaying from your IP address
  • Authentication is required but not configured

Solutions:

  1. Ensure you've entered username and password
  2. Contact your email provider to confirm your account has SMTP access
  3. Some corporate email systems block SMTP relay (use OAuth Gmail instead)

Error: "SSL/TLS handshake failed"

Possible Causes:

  • Wrong encryption setting (TLS vs SSL)
  • Outdated SSL certificate
  • Man-in-the-middle security software (corporate antivirus)

Solutions:

  1. Try TLS instead of SSL, or vice versa
  2. Update your browser and operating system
  3. If on corporate network, ask IT if there's a proxy or antivirus blocking SMTP

Client Not Receiving Emails​

If a specific client says they never receive your emails:

Step 1: Verify Email Address

Check for Typos:

  • Extra spaces before/after email
  • Wrong domain (.com vs .net, .org vs .co)
  • Swapped letters (gmai.com vs gmail.com)
  • Missing or extra dots (john.doe vs johndoe)

Test the Email: Send a test email from your personal email to their address. If it bounces back, the address is wrong.

Step 2: Check Email Logs

  1. Go to Settings → Integrations → Email → Recent Emails
  2. Find emails sent to that client
  3. Check status:
    • Bounced: Email address doesn't exist or mailbox full
    • Delivered: Email reached their server (check spam)
    • Failed: See error message for details

Step 3: Ask Client to Whitelist

Provide these instructions:

  • Add your email address to their contacts
  • Create filter to move your emails to inbox
  • Check spam/junk folder

Step 4: Use Alternative Email

If client has multiple email addresses:

  • Try sending to their alternate email
  • Ask if they prefer personal vs work email
  • Some clients' work emails block external messages

Step 5: Send Via Personal Email

As a last resort:

  • Send from your personal Gmail/Outlook directly (outside ShootPath)
  • Include the invoice/quote as an attachment
  • Mark it as sent in ShootPath manually

Email Template Problems​

If email templates aren't loading or sending:

Template Variables Not Replacing:

Example: Email shows "{{client_name}}" instead of "John Smith"

Cause: Template syntax error or missing data.

Solution:

  1. Go to Settings → Email Templates
  2. Click the template having issues
  3. Check variable syntax: {{variable_name}} (two curly braces, no spaces)
  4. Common variables:
    • {{client_name}}
    • {{job_type}}
    • {{quote_total}}
    • {{invoice_due_date}}
  5. Save template
  6. Send test email to yourself

Template Formatting Broken:

Email appears with weird formatting, missing line breaks, etc.

Cause: HTML formatting issue.

Solution:

  1. Edit template
  2. Click the Source button to view HTML
  3. Look for unclosed tags (div tags without closing tags)
  4. Simplify formatting (remove complex HTML)
  5. Save and test

Attachments Not Included:

Quote or invoice PDF not attaching to email.

Cause: Attachment generation failed.

Solution:

  1. Check Settings → Integrations → Email → Recent Emails
  2. Find the email
  3. If error mentions "PDF generation failed":
    • Quote/invoice template may have errors
    • Try regenerating the quote/invoice
    • Contact support if it persists

Common Questions​

Why do my emails go to spam even though I'm using Gmail? Sending from a Gmail address (yourname@gmail.com) can still trigger spam filters if:

  • You're sending to corporate emails with strict filters
  • Your email content looks like marketing/spam
  • You're sending to many recipients at once

Use a custom domain (yourname@yourbusiness.com) for better deliverability.

Can I use my existing email address? Yes! You can use:

How many emails can I send per day?

  • Gmail free: 500 emails/day
  • Google Workspace: 2,000 emails/day
  • SMTP providers: Varies (SendGrid, Mailgun have higher limits)

Most photographers send fewer than 50 emails/day, so Gmail free is usually enough.

Do clients see my email address? Yes, emails come FROM your email address (the one you connected in Settings → Integrations). Replies from clients come back to your email inbox.

Can I change the "From" name? Yes:

  1. Go to Settings → Business Information
  2. Update Business Name
  3. Emails will show as: "Business Name" with your email address

What if Gmail blocks my account? If Gmail suspects unusual activity:

  • You'll receive an email: "Suspicious activity blocked"
  • Click Yes, it was me to confirm
  • Reconnect Gmail in ShootPath

If your account is permanently blocked, contact Google support or switch to SMTP.

Can I use multiple email addresses? Currently, ShootPath only supports one email integration at a time. If you have multiple businesses, either:

  • Use one email for all
  • Switch email integration when needed (disconnect old, connect new)
  • Create separate ShootPath accounts

Why does it take a few minutes for emails to send?

  • ShootPath queues emails to avoid overloading email servers
  • Most emails send within 1-2 minutes
  • During high usage, may take up to 5 minutes
  • Check email logs to confirm sending

Still Having Email Issues?​

Contact Support:

For ShootPath Email Integration: Email support@shootpath.com

  • Include: Email logs screenshots, error messages, steps you tried

For Gmail Account Issues: Contact Google support: support.google.com/mail

For SMTP Provider Issues: Contact your email provider's support (SendGrid, Mailgun, etc.)

We're here to help get your emails delivering reliably!