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Sending email

Esqase lets you send email to clients and colleagues straight from a matter, a lead, or a contact, using your own connected Gmail account. Every message you send is logged on the Communications tab so your whole team can see the conversation history, and replies sync back into the same record automatically. This page covers composing and sending email, choosing which matter or lead a contact's email is filed under, applying templates, working with your signature and placeholders, and saving and retrying drafts.

Before you begin

A few things make the email composer work the way you expect:

  • A connected Google (Gmail) account. Esqase sends each email through the sender's own Gmail, so you must link your Google account first. If you have not, the composer shows a connect prompt instead of the form (see The connect-Gmail-first path). See Connecting Google (Gmail, Calendar, Meet).
  • Create access for communications. You see the New button and the Send email option only if your role includes Create access for communications. If your role is view-only, you can read the log but not compose. See Roles and permissions.
  • An open matter, lead, or contact. Email is composed in the context of a matter (on its Communications tab), a lead (from the lead's header), or a contact (from the contact's detail page). The matter or lead's client contacts (or the contact you opened) are pre-loaded as suggested recipients.

Note: The address you send from is your linked Gmail address. It appears in the read-only From field and cannot be changed in the composer. If you want to send from a different address, link that Google account instead.

Open the email composer

You can start an email from four places.

From the header (anywhere):

  1. Click the + button on the right of the dashboard header.
  2. Click Send email.

This opens the composer with a required Link to field at the top of the form. Pick any active matter or open lead — the email is then logged on that record's Communications tab. The field is only shown when your firm has at least one active matter or open lead to link to; if there are none, it is hidden and the email is filed firm-wide. To always have the record pre-filled without being asked, open the composer from a matter, lead, or contact instead. See Navigating the dashboard.

From a matter:

  1. In the sidebar, click Matters, then open the matter you want.
  2. Click the Communications tab.
  3. Click New, then choose Send email.

From a lead:

  1. In the sidebar, click Leads (under intake), then open the lead.
  2. In the lead header, click Send email.

From a contact:

  1. In the sidebar, click Contacts, then open the contact you want.
  2. In the contact header, click Send email.

The Send email dialog opens. Its description confirms the scope: "Send an email from your synced Gmail. It is logged against this matter (or lead, or contact) and replies sync back automatically."

When you open the composer from a contact, the email is not tied to a matter or lead on its own. Instead, the form shows a Link to picker so you can choose which of the contact's matters or leads to file the email under. See Choose which matter or lead a contact's email is filed under.

📷 Screenshot: The matter Communications tab with the New dropdown open, showing Send email, Email log, and Phone log. Highlight the Send email item. Suggested image: images/sending-email/open-composer-new-menu.png

Send an email through your connected Gmail

Once the Send email dialog is open, compose your message in the form fields, then send it. The whole message goes out through your Gmail, so it lands in your real Sent folder and threads normally for the recipient.

  1. From is filled in for you with your connected Gmail address and is read-only.
  2. In the To field, add one or more recipients. Click in the field and a list opens with two groups, Members (people at your firm, each shown with their email) and Contacts (your firm's contacts, each shown with the email on their record). You can:
    • Pick a member of your firm from the list.
    • Pick any contact in your firm from the list. When you opened the composer from a matter or lead, that record's client contacts who have an email are added for you automatically; when you opened it from the header + menu, the To field starts empty so you choose the recipients yourself.
    • Type any email address, then press Enter or click the Use '…' option at the bottom of the list to add it. Esqase checks that it looks like a valid email and shows a short hint if it does not. Start typing to filter the list by name or email. Each recipient appears as a removable chip. Click the small x on a chip, or press Backspace in an empty field, to remove the last one.
  3. To copy other people, click Add Cc/Bcc, then fill in the Cc and Bcc fields the same way. Both accept more than one recipient.
  4. (Optional) Pick a Template to prefill the subject and body. See Apply an email template.
  5. In Subject, type the email subject (up to 255 characters). This field is required.
  6. In Body, write your message using the rich text editor. Your signature is already inserted at the bottom (see Insert and edit your signature). This field is required.
  7. Click Send.

While the email is sending, the button shows a spinner and reads Sending.... On success you see a Email sent confirmation, the dialog closes, and the message appears as a new row on the Communications tab with the status Active.

Note: If your subject or body still contains a placeholder that was not filled in when you click Send, Esqase asks you to confirm before the email goes out. See Confirm unfinished placeholders before sending.

📷 Screenshot: The Send email dialog filled out, showing From (read-only), recipient chips in To, the Template picker, Subject, and the Body editor with a signature. Highlight the Send button. Suggested image: images/sending-email/send-email-dialog.png

Important: Esqase saves the email as a record before it tries to send. If the Gmail send fails for any reason, the message is kept as a draft so you can retry it without retyping (see Retry a failed send).

Tip: You can set the composer aside without losing your work. Click the minimize button (the - icon) next to the close (x) button to collapse it into a small bar in the bottom-right corner, then click the bar to bring it back with your draft intact. You cannot minimize or close the composer while it is sending or saving. See Navigating the dashboard.

Choose which matter or lead the email is filed under

The Link to picker appears in two situations: when you open the composer from the header + menu, and when you open it from a contact's detail page. In both cases it lets you decide where the email is logged so it lands on the right record's Communications tab.

When you open the composer from a matter or lead directly, the email is already filed against that record and the Link to picker is not shown.

From the header + menu

  1. In the Send email dialog opened from the header + menu, the Link to field is at the very top of the form and is required.
  2. Open the picker. It lists all of your firm's active matters and open leads.
  3. Pick the matter or lead you want the email filed under. You must select one before the form will submit.

From a contact's detail page

When you compose from a contact's detail page, the email is not automatically attached to a matter or lead, because a contact can be a client on several matters or tied to more than one lead.

  1. In the Send email dialog, find the Link to field at the top of the form. It is required when the contact has at least one matter or open lead on file.
  2. Open the picker. It lists:
    • The contact's active client matters, each shown by its number and title, for example 00123 - Acme acquisition.
    • The contact's open leads that have not been converted to a matter yet, each shown as Lead followed by its number, for example Lead 00045.
  3. Pick the matter or lead you want the email filed under. If the contact has exactly one matter (and no open leads), or exactly one open lead (and no matters), that one is selected for you automatically. You can change it.
  4. If the contact has no matters and no open leads, the Link to field is hidden. The email sends and is logged against the contact, but does not appear on a matter or lead Communications tab.

When you send, the email is logged on the Communications tab of whichever matter or lead you chose, alongside emails sent from that record directly. Replies still sync back into the same place.

Note: If the Link to field does not appear, the contact has no active matters and no open leads yet, so there is nothing to link to. The email still sends and is logged against the contact.

Tip: If you file a contact's email under a lead and that lead is later converted to a matter, the email follows the conversion and appears on the new matter's Communications tab automatically.

📷 Screenshot: The Send email dialog showing the Link to picker open with matters and leads listed and one option selected. Suggested image: images/sending-email/link-to-picker.png

What happens to recipients with no email on file

If you pick a contact who has no email address saved (in To, Cc, or Bcc), Esqase shows a No email on file dialog instead of adding them. It tells you the contact has no email and offers a Go to contact link. Open the contact, add an email, then come back and pick the contact again. See Working with contacts.

Apply an email template

A template is a reusable, pre-written email (subject and body) your firm has set up, for example an engagement-letter cover note or an appointment reminder. Applying one saves you from writing the same message twice.

  1. In the Send email dialog, open the Template field.
  2. Pick a template from the list. The field is labeled Pick a template to prefill.
  3. Esqase fills the Subject and Body with the template's content, resolves any placeholders against the current contact, member, firm, and date, and appends your signature.
  4. Edit the prefilled text however you like.

Note: If you change the subject or body by hand after applying a template, the Template selection clears. That is expected: it just means the message no longer matches the template exactly. Your edits are kept.

Tip: If the Template field reads No templates available, your firm has not created any email templates yet. A firm member with the right access can add them under settings. See Email templates.

📷 Screenshot: The Template dropdown open in the Send email dialog with a list of templates. Highlight one selected template and the prefilled Subject below. Suggested image: images/sending-email/apply-template.png

Insert and edit your signature

Your email signature (the closing block with your name, firm, and contact details) is added automatically every time you open the composer or apply a template. It is inserted directly into the Body editor, below your message, so you can see and edit it inline before sending.

  • The signature is your personal signature if you have set one, otherwise your firm's default signature.
  • Placeholders inside the signature (such as your name and the firm address) are filled in for you when it appears in the editor.
  • Because the signature lives in the Body field, you can change it for this one email, delete it, or reorder it just like any other text. Editing it here does not change your saved signature.

To change the signature for every future email instead of just this one, update it in your settings. See Email signatures.

Tip: If you do not want a signature on a particular email, simply delete the signature block from the Body before sending.

Use template placeholders

Placeholders are short keys you wrap in double braces, like {{contact_firstname}}. Esqase replaces them with real values at send time so a single template can greet each recipient by name. You can type placeholders anywhere in the Subject or Body.

At the bottom of the composer is an Available placeholders panel. Click See more to expand the full list of keys, grouped by category. Hover any key to see what it inserts.

How placeholders behave:

  • Wrap each key in double braces, for example {{contact_name}} or {{firm_phone}}.
  • They are replaced when you send (or save a draft). The recipient never sees the braces.
  • If a key has no value (for example, the contact has no phone on file) or the key is misspelled, Esqase leaves it unchanged rather than inserting a blank. When you click Send, Esqase warns you about any placeholders that were left unfilled so you can finish them first (see Confirm unfinished placeholders before sending).
  • The contact placeholders resolve against the first contact in your To list, falling back to the matter or lead's primary contact.

The most common groups you will use:

  • Contact (the person you are writing to): contact_name, contact_prefix, contact_firstname, contact_middlename, contact_lastname, contact_suffix, contact_email, contact_phone, contact_address.
  • Firm: firm_name, firm_email, firm_phone, firm_address.
  • Member (sender), meaning you: member_name, member_firstname, member_lastname, member_email, member_phone, and more.
  • Today: date_today (today's date) and time_today (the current time).

Note: Other groups (such as Event, Form, Invoice, and Document) appear in the list too. Those keys are filled in only when Esqase sends the email as part of a workflow or scheduling step that has that context. In a plain email you compose by hand, they may be left unchanged.

📷 Screenshot: The Available placeholders panel expanded (after clicking See more), showing the Contact, Firm, Member (sender), and Today groups with their keys. Suggested image: images/sending-email/placeholders-expanded.png

Confirm unfinished placeholders before sending

Esqase checks your message when you click Send. If the Subject or Body still contains a placeholder that was not filled in (for example {{firm_address}} when no firm address is on file, or a key with a typo), a Finish your placeholders before sending dialog appears before anything is emailed. It:

  • Warns that the email still has placeholder values that were not filled in, and that they will be sent exactly as written.
  • Lists each leftover placeholder, such as {{firm_address}}, so you can see what to fix.
  • Points out that an unrecognized key is usually a typo you should correct or remove.

You then choose:

  • Go back and edit closes the dialog without sending, so you can fill in the value, pick the matching contact, or fix the key, then click Send again.
  • Send anyway sends the email as written, leaving the placeholder text in the message.

This check runs only when you click Send. Saving a draft never shows it, so you can keep unfinished placeholders in a draft and resolve them later.

📷 Screenshot: The Finish your placeholders before sending dialog listing one or more leftover placeholder chips such as {{firm_address}}, with the Go back and edit and Send anyway buttons. Suggested image: images/sending-email/unfinished-placeholders-confirm.png

Save an email as a draft

If a message is not ready to send, save it as a draft and finish it later. Drafts are kept on the Communications tab so you (or a colleague with access) can pick them back up.

  1. Compose the email as usual: add recipients, a subject, and a body.
  2. Instead of Send, click Save draft.

The button shows Saving... while it works, then you see a Draft saved confirmation and the dialog closes. The message appears on the Communications tab with the status Draft. Nothing is emailed yet.

Tip: You do not have to fill in everything to save a draft. Save early and often, then come back when you have the missing details.

Open and send a saved draft later

  1. On the matter's Communications tab, find the row with the Draft status. (Drafts are hidden by the default filter, which shows Active only. Use the Status filter and select Draft to show them.)
  2. In that row's actions, click Edit. The Send email dialog reopens with the title Edit draft email and your saved recipients, subject, and body restored.
  3. Make any final changes.
  4. Click Send to send it now, or Save draft again to keep editing later.

📷 Screenshot: The Communications tab with the Status filter open and Draft selected, and a draft row showing its Edit button. Suggested image: images/sending-email/find-and-edit-draft.png

Retry a failed send from a saved draft

Because Esqase saves the email record before contacting Gmail, a failed send never loses your work. If the send fails, you see the message "We couldn't send through Gmail. The draft was saved so you can try again," and the message is kept as a Draft on the Communications tab.

To retry:

  1. Open the matter's Communications tab.
  2. Show drafts using the Status filter (select Draft), then find the failed message.
  3. Click Edit to reopen it in the Send email dialog.
  4. Confirm the recipients, subject, and body still look right.
  5. Click Send again.

If the send succeeds this time, the row flips from Draft to Active and the email goes out.

Note: A common reason a send fails is that your Gmail connection has expired or been revoked. If retries keep failing, reconnect your Google account, then try again. See Connecting Google (Gmail, Calendar, Meet).

The connect-Gmail-first path (when Gmail is not connected)

If you have not linked a Google account yet, you cannot send email from Esqase, so the composer guides you to connect first.

  1. Open the Send email dialog from anywhere it appears: the header + menu, a matter, a lead, or a contact.
  2. Instead of the compose form, you see a notice titled Connect your Gmail to send email, explaining that you need to link your Gmail account before you can send and log emails, and that replies will then sync back automatically.
  3. Click Go to integrations.
  4. On the integrations page, connect your Google (Gmail) account, then open Send email again. The compose form now appears.

📷 Screenshot: The Send email dialog showing the Connect your Gmail to send email notice with the Go to integrations link. Highlight the link. Suggested image: images/sending-email/connect-gmail-first.png

For the full connection steps, see Connecting Google (Gmail, Calendar, Meet).

Emails Esqase sends for you also appear on Communications

Beyond the emails you write in the composer, Esqase sends a few emails on your behalf as part of other flows. When one of those emails relates to a matter or lead, it is recorded on that record's Communications tab too, so the tab shows the full picture of what your client has been sent. You do not have to do anything: these rows appear on their own and are read-only.

These automatic rows cover:

  • Invoice payment notices. When you email a client a payment link from an invoice, the message is filed on that invoice's matter. See Creating and sending invoices.
  • Document share links. When you share a document with a specific recipient, the secure link is emailed to them and recorded on the document's matter. See Sharing documents.
  • Signature request links. When you send a document for signature, each outside signer's signing link is emailed to them and recorded on the matter. See Requesting e-signatures.
  • Booking and payment sign-in links. When a client asks for a secure sign-in link to open a booking page or a payment link, that email is recorded on the related matter or lead.

Note: These rows behave like any other sent email on the tab: they are read-only, show the Email type, and can be searched and filtered along with everything else. They appear only when the email is connected to a matter or lead.

Common questions

Where do sent emails go after I send them? Each email becomes a row on the Communications tab of the matter or lead it is filed under, with the Email type. When you send from a contact, that is whichever matter or lead you chose in the Link to picker. Sent emails are read-only there. Replies from the recipient sync back into the same record automatically, so the thread stays in one place.

I sent an email from the header + menu (or from a contact). Why did it ask me what to link it to? When there is no specific matter or lead already in scope, Esqase cannot guess which record the email belongs to. The Link to picker lets you choose, or you can leave it Not linked to a matter or lead. When composing from a contact, the picker shows only that contact's matters and leads. From the header +, it shows all active firm matters and open leads. See Choose which matter or lead the email is filed under.

Can I edit an email after I send it? No. Once an email has been sent through Gmail it becomes read-only in Esqase, so you can only View it, not edit it. Only drafts can be edited. To follow up, send a new email.

Why is the From field locked? Esqase sends as you, from your own connected Gmail, so the From address is fixed to your linked account. This keeps the email genuine for the recipient and keeps replies threading back correctly.

Someone added a contact's email after I started. Do I need to start over? No. Close the No email on file notice, add the email on the contact, then reopen the composer and pick the contact again.

Why did Esqase ask me to confirm placeholders when I clicked Send? Your message still had a placeholder that was not filled in, such as {{firm_address}} with no value on file or a key with a typo. Esqase pauses so the braces do not go out by accident. Choose Go back and edit to fix it, or Send anyway to send it as written. See Confirm unfinished placeholders before sending.

Troubleshooting

  • I don't see a New button or a Send email option. Your role may not include Create access for communications, or you may not have permission to view the Communications tab. Ask a firm owner or administrator to adjust your role. See Roles and permissions.
  • The composer shows a connect notice, not the form. Your Google account is not linked. Click Go to integrations and connect it. See Connecting Google (Gmail, Calendar, Meet).
  • My placeholder did not get replaced. The key may be misspelled, or the underlying value may be empty (for example, the contact has no phone). Esqase leaves unknown or empty keys as-is. Open Available placeholders, click See more, and copy the exact key. When you click Send, Esqase also lists any leftover placeholders so you can fix them before the email goes out.
  • A dialog asked me to finish my placeholders. Your message still has a placeholder that was not filled in. Choose Go back and edit to fix it, or Send anyway to send the message as written. See Confirm unfinished placeholders before sending.
  • The Template field says "No templates available." Your firm has no email templates yet. See Email templates.
  • The send failed. Your message was saved as a draft. Reopen it from the Communications tab (filter by Draft), click Edit, and click Send again. If it keeps failing, reconnect Google.