Summary

JQL searches ignore custom fields contexts when sorting. The only value taken in consideration is the option sequence number in the database.

Steps to Reproduce

1. Create two projects, called ONE and TWO.
2. Create a custom field with type Select List (multiple choices) named Country.
3. Add a context for each project (ONE and TWO) and add options to each context in the following way:
   
4. Create issues on both projects, randomly assigning values of Country to each issue. The script below might help:

   #!/bin/bash
   USERNAME="admin"
   PASSWORD="admin"
   BASE_URL="http://localhost:8080"
   URL="$BASE_URL/rest/api/2/issue/"
   KEY="TWO"
   AMOUNT=25
   for i in $(seq $AMOUNT)
   do
     COUNTRY=$(shuf -n1 -e 'Malaysia' 'Indonesia' 'Hong Kong' 'China' 'Thailand')
     DATA="{ \"fields\": { \"project\": { \"key\": \"$KEY\" }, \"summary\": \"Task #$i\", \"description\": \"Task #$i \", \"customfield_10007\": [{ \"value\":\"$COUNTRY\" }], \"issuetype\": { \"name\": \"Task\" } } }"
     curl -u $USERNAME:$PASSWORD -X POST --data "$DATA" -H 'Content-Type: application/json' $URL
     echo
   done
   

5. Run the following JQL query:

   issuetype = Task ORDER BY Country ASC
   

Expected Results

All issues are sorted by their value of Country, in alphabetical order.

Actual Results

Issues are displayed out of order in regard to to the field Country, like in the example below:

Workaround

None