#The following works fine:

library(httr) #http
library(emayili) #email
library(stringr) #string manipulation

smtp_server <- Sys.getenv("SMTP_SERVER")
smtp_port <- Sys.getenv("SMTP_PORT")
smtp_username <- Sys.getenv("SMTP_USERNAME")
IP <- content(GET("https://api.ipify.org?format=json"))$ip

smtp <- server(
  host = smtp_server,
  port = smtp_port,
  username = smtp_username,
  password = Sys.getenv("SMTP_PASSWORD"),
  max_times = 1
)

envelope(
  to = "[email protected]",
  from = smtp_username,
  subject = str_c("This is a plain text message!", IP, Sys.time()),
  text = "Hello!"
) |>
smtp()

#The following results in a fatal error though, aborting the r Studio session

library(shiny)
library(httr)
library(emayili)

smtp_server <- Sys.getenv("SMTP_SERVER")
smtp_port <- Sys.getenv("SMTP_PORT")
smtp_username <- Sys.getenv("SMTP_USERNAME")

IP <- content(GET("https://api.ipify.org?format=json"))$ip

smtp <- server(
  host = smtp_server,
  port = smtp_port,
  username = smtp_username,
  password = Sys.getenv("SMTP_PASSWORD"),
  max_times = 1
)

ui <- fluidPage(
  titlePanel("{emayili} & Shiny"),
  tags$head(
    tags$style(HTML("
      body {
        background-color: black;
        color: white;
      }
      td {
        padding-left: 10px;
      }
    "))
  ),
  fluidRow(
    column(
      width = 6,
      tags$table(
        tags$tr(
          tags$th("{emayili version}:"),
          tags$td(as.character(packageVersion("emayili")))
        ),
        tags$tr(
          tags$th("IP address:"),
          tags$td(IP)
        ),
        tags$tr(
          tags$th("SMTP server:"),
          tags$td(smtp_server)
        ),
        tags$tr(
          tags$th("SMTP port:"),
          tags$td(smtp_port)
        )
      )
    ),
    column(
      width = 6,
      class = "text-center",
      actionButton(
        "send",
        "Send Message",
        icon = icon("envelope"),
        class = "btn-primary"
      )
    )
  )
)

server <- function(input, output, session) {
  observeEvent(input$send, {
   message("Sending message to ", smtp_username, ".")
    envelope(
      to = smtp_username,
      from = smtp_username,
      subject = strftime(Sys.time(), "{emayili} & Shiny [%F %X]")
    ) %>%
      text("This message was sent from Shiny on {{ IP }} using {emayili}.") %>%
      smtp()
   })
 }

shinyApp(ui = ui, server = server)

#Both use the same .Renviron file.
#R 4.4, R Studio 2024.04.2 Build 764

Running the script works ok, but the shiny app crashes.
I tried reinstalling R and reinstalling all libraries.

I have a large app that sends results to the user using emayily. This worked flawlessly until lately, also when deployed on shinyapps.io. Now, it crashes, and I managed to isolate it. Sending the mail from the app, locally on my macbook Apple M3 Pro, 36GB results in the error. The deployed version works fine.