create-outlook-draft

name	create-outlook-draft
compatibility	Requires Windows with the classic Outlook desktop client and PowerShell 5.1+ for COM automation.
description	Create Outlook email drafts from Markdown email files via COM automation in PowerShell. Parses metadata tables (To, CC, Subject) from Markdown, converts Markdown body to styled HTML (tables, bold, lists), and saves drafts to the Outlook Drafts folder. Handles COM lifecycle, locked items, duplicate cleanup, and batch processing of multiple email files. USE FOR: create draft, Outlook draft, email draft, draft email, batch drafts, markdown to email, md to Outlook, create email from markdown, reminder email, save draft, Outlook Drafts folder, bulk email drafts, convert markdown email. DO NOT USE FOR: sending emails (use send-outlook-email skill), reading email (use outlook-email-export skill), calendar invites, Exchange Web Services, Microsoft Graph API.

Create Outlook Draft from Markdown

Skill for creating Outlook email drafts from Markdown email files via COM automation.

When to Use

• Create one or more email drafts in Outlook from Markdown .md files
• Convert Markdown-formatted emails (with metadata tables) to properly styled HTML drafts
• Batch-process a folder of reminder/notification emails into Outlook Drafts

Prerequisites

• Microsoft Outlook must be installed and configured
• The Outlook COM API (Outlook.Application) must be accessible from PowerShell
• Windows only (COM technology)

Expected Markdown Email Format

Each .md file must contain a metadata table followed by the email body:

# Email Title

| Field | Value |
|-------|-------|
| **Folder** | Outbox |
| **Date** | 2026-04-19 |
| **From** | Sender Name <[e-mail]> |
| **To** | Recipient One <[e-mail]>; Recipient Two <[e-mail]> |
| **CC** | CC Person <[e-mail]> |
| **Subject** | Your Email Subject Here |

Dear Team,

Email body in **Markdown** format with tables, lists, etc.

Best regards,
Sender Name

Critical Lessons Learned

1. Always Write to a .ps1 Script File First

The VS Code integrated terminal swallows output from complex inline scripts with here-strings, HTML, and multi-line content. NEVER run complex Outlook COM scripts inline. Always write the script to a .ps1 file first, then execute it:

# Write script to file, execute, read results, clean up
$scriptContent | Set-Content 'path\script.ps1' -Encoding UTF8NoBOM
& 'path\script.ps1'
Get-Content 'path\results.txt'
Remove-Item 'path\script.ps1', 'path\results.txt' -Force

2. Use [regex]::Match() — Never PowerShell -match with **

The metadata table contains **To**, **CC**, **Subject**. PowerShell interprets ** as a glob pattern when used with -match. ALWAYS use the [regex] class:

# CORRECT — [regex] class bypasses PowerShell glob interpretation
$rTo   = [regex]::Match($content, '\|\s+\*{2}To\*{2}\s+\|\s+(.+?)\s*\|')
$rCC   = [regex]::Match($content, '\|\s+\*{2}CC\*{2}\s+\|\s+(.+?)\s*\|')
$rSubj = [regex]::Match($content, '\|\s+\*{2}Subject\*{2}\s+\|\s+(.+?)\s*\|')

$toRaw   = if ($rTo.Success)   { $rTo.Groups[1].Value.Trim() } else { '' }
$ccRaw   = if ($rCC.Success)   { $rCC.Groups[1].Value.Trim() } else { '' }
$subject = if ($rSubj.Success) { $rSubj.Groups[1].Value.Trim() } else { $f.BaseName }

3. Extract Email Addresses from Name <email> Format

Recipients in Markdown use Name <[e-mail]> format. Extract only the email addresses for the Outlook COM API:

$toEmails = ([regex]::Matches($toRaw, '<([^>]+@[^>]+)>') |
             ForEach-Object { $_.Groups[1].Value }) -join '; '

# Fallback for plain addresses without angle brackets
if (-not $toEmails -and $toRaw -match '@') {
    $toEmails = ($toRaw -split ';' |
                 ForEach-Object { $_.Trim() } |
                 Where-Object { $_ -match '@' }) -join '; '
}

4. Use .Save() NOT .Send() for Drafts

$mail = $ol.CreateItem(0)
$mail.To      = $toEmails
if ($ccEmails) { $mail.CC = $ccEmails }
$mail.Subject = $subject
$mail.HTMLBody = $html
$mail.Save()    # Saves to Drafts folder — does NOT send

5. Handle Locked Items with Try/Catch

Outlook locks items open in the editor. Always wrap .Delete():

foreach ($item in $toDelete) {
    try {
        $item.Delete()
    } catch {
        # Item is open in Outlook — skip and retry later
    }
}

6. Subject Line Trailing Pipe Bug

When the regex for Subject extraction does not trim the trailing | from the Markdown table, Outlook saves it as part of the subject. Always use non-greedy match with explicit pipe boundary:

# CORRECT — non-greedy, trims trailing pipe
$rSubj = [regex]::Match($content, '\|\s+\*{2}Subject\*{2}\s+\|\s+(.+?)\s*\|')

# WRONG — greedy match captures the trailing pipe
$rSubj = [regex]::Match($content, '\|\s+\*{2}Subject\*{2}\s+\|\s+(.+)')

Converting Markdown Body to HTML

Basic Conversion (Plain Text with Bold)

# Extract body: everything after the Subject row in the metadata table
$bodyStarted = $false
$bodyLines = @()
foreach ($line in ($content -split "`n")) {
    if ($bodyStarted) { $bodyLines += $line }
    elseif ($line -match '\*{2}Subject\*{2}') { $bodyStarted = $true }
}
$bodyText = ($bodyLines -join "`n").Trim()

# Markdown bold to HTML strong
$htmlBody = [regex]::Replace($bodyText, '\*{2}(.+?)\*{2}', '<strong>$1</strong>')
$htmlBody = $htmlBody -replace "`n`n", '</p><p>'
$htmlBody = $htmlBody -replace "`n", '<br/>'
$htmlBody = "<p>$htmlBody</p>"

$fullHtml = "<html><body style='font-family:Segoe UI,Arial,sans-serif;color:#333;line-height:1.6;max-width:700px;'>$htmlBody</body></html>"

Markdown Tables → Styled HTML Tables

Markdown tables render as raw pipe characters in Outlook. The basic conversion above CANNOT handle tables. When a markdown email contains a table, build the full HTML for that specific draft directly in the script:

<table style="border-collapse:collapse;width:100%;margin:12px 0;">
<tr style="background-color:#2E7D32;color:#fff;">
  <th style="border:1px solid #ddd;padding:8px 12px;text-align:left;">Col 1</th>
  <th style="border:1px solid #ddd;padding:8px 12px;text-align:left;">Col 2</th>
</tr>
<tr>
  <td style="border:1px solid #ddd;padding:8px 12px;">Value 1</td>
  <td style="border:1px solid #ddd;padding:8px 12px;">Value 2</td>
</tr>
<tr style="background-color:#f9f9f9;">
  <td style="border:1px solid #ddd;padding:8px 12px;">Value 3</td>
  <td style="border:1px solid #ddd;padding:8px 12px;">Value 4</td>
</tr>
</table>

Style conventions:

• Header row: background-color:#2E7D32 (green), color:#fff (white text)
• Alternating data rows: every other <tr> gets background-color:#f9f9f9
• All cells: border:1px solid #ddd; padding:8px 12px
• Use <th> for header cells, <td> for data cells

Deleting Existing Drafts Before Recreation

To avoid duplicates when re-running, delete existing drafts by subject pattern:

$ns = $ol.GetNamespace('MAPI')
$drafts = $ns.GetDefaultFolder(16)  # olFolderDrafts = 16

# Collect first, then delete — deleting during enumeration skips items
$toDelete = @()
foreach ($item in $drafts.Items) {
    if ($item.Subject -match 'REMINDER') {
        $toDelete += $item
    }
}
foreach ($item in $toDelete) {
    try { $item.Delete() } catch { <# item locked — skip #> }
}

Important: Collect items into an array first, then delete in a separate loop. Deleting during enumeration changes the collection and skips items.

Updating an Existing Draft

Find a draft by subject and replace its HTML body:

foreach ($item in $drafts.Items) {
    if ($item.Subject -match 'Shipping Instructions') {
        $item.HTMLBody = $newHtml
        $item.Save()
        break
    }
}

Use -match (regex) for subject matching — it handles both – (em-dash) and - (hyphen) without issues, unlike -eq exact match.

Always Release COM Objects

[System.Runtime.InteropServices.Marshal]::ReleaseComObject($mail)   | Out-Null
[System.Runtime.InteropServices.Marshal]::ReleaseComObject($drafts) | Out-Null
[System.Runtime.InteropServices.Marshal]::ReleaseComObject($ns)     | Out-Null
[System.Runtime.InteropServices.Marshal]::ReleaseComObject($ol)     | Out-Null

Troubleshooting

Symptom	Cause	Fix
Subject ends with |	Greedy regex captured trailing pipe	Use non-greedy (.+?) with \s*| boundary
Terminal shows no output	Complex here-strings swallowed by VS Code terminal	Write to .ps1 file first, then execute
Outlook cannot delete this item	Draft is open in Outlook editor	Close the draft in Outlook, retry
Duplicate drafts after re-run	Old drafts not cleaned up	Delete by subject pattern before creating
** parsed as glob in regex	PowerShell interprets \*\* as glob	Use \*{2} or [regex]::Match()
HTML table shows as raw pipes	Markdown table not converted	Build HTML table directly in script
Empty CC causes error	Blank CC string is fine, $null is not	Guard: if ($ccEmails) { $mail.CC = $ccEmails }
COM object leak	References not released	Always call ReleaseComObject() on all COM objects