IIS Express certs (for now) don't contain SAN strings. This makes Chrome unhappy. Make Chrome happy again with a new organic, artisanal, gluten free HTTPS certificate.

UpdateIISExpressSSLForChome.ps1

# Create a new self signed HTTPS Certificate for IIS Express
# Crafted with all organic, GMO, gluten free ingreditations 
# with an artisinal SAN to make Chrome 58 onwards happy.
#
# See https://bugs.chromium.org/p/chromium/issues/detail?id=308330
#
# Run this at an administrative PowerShell prompt.
#
# You will be prompted to trust a new certificate via a windows dialog.
# Click yes otherwise Visual Studio will not be able to determine your
# process ID when you launch your web application/
#
# SCRIPT PROVIDED "AS IS" WITHOUT WARRANTY OF ANY KIND, EITHER EXPRESSED OR IMPLIED.

$certificate = New-SelfSignedCertificate `
    -Subject localhost `
    -DnsName localhost `
    -KeyAlgorithm RSA `
    -KeyLength 2048 `
    -NotBefore (Get-Date) `
    -NotAfter (Get-Date).AddYears(5) `
    -CertStoreLocation "cert:CurrentUser\My" `
    -FriendlyName "IIS Express Development Certificate" `
    -HashAlgorithm SHA256 `
    -KeyUsage DigitalSignature, KeyEncipherment, DataEncipherment `
    -TextExtension @("2.5.29.37={text}1.3.6.1.5.5.7.3.1") 
$certificatePath = 'Cert:\CurrentUser\My\' + ($certificate.ThumbPrint)    

# Now export the certificate to a pfx
$pfxPassword = ConvertTo-SecureString ([Guid]::NewGuid().ToString()) -Force -AsPlainText
$pfxFilePath =  [system.io.path]::GetTempFileName()
$cerFilePath = [system.io.path]::GetTempFileName()

Export-PfxCertificate -Cert $certificatePath -FilePath $pfxFilePath -Password $pfxPassword
Export-Certificate -Cert $certificatePath -FilePath $cerFilePath

# Delete the cert we created from the user store now we've exported it
Remove-Item $certificatePath

# Now pull in the PFX to the two places it needs to be.
# First to the machine personal store, so netsh can bind
Import-PfxCertificate -FilePath $pfxFilePath Cert:\LocalMachine\My -Password $pfxPassword -Exportable

# Now to the user root store so trust is enabled
# This will cause Windows to throw up a dialog, so click yes, otherwise VS is going to be very unhappy and unable to determine your app process ID.
Import-Certificate -FilePath $cerFilePath -CertStoreLocation Cert:\CurrentUser\Root

# Now bind using netsh. The app ID is the IIS Express app ID.
for ($port = 44300; $port -lt 44400; $port++)
{
    $command = "http delete sslcert ipport=0.0.0.0:$port"
    Write-Output $command
    $command | netsh
    
    $command = "http add sslcert ipport=0.0.0.0:$port certhash="+$($certificate.Thumbprint)+" appid={214124cd-d05b-4309-9af9-9caa44b2b74a}"
    Write-Output $command
    $command | netsh
}

# Clean up the temporary PFX
Remove-Item $pfxFilePath
Remove-Item $cerFilePath