Selfhosted
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Like others said it's mostly just practice.
What helps is to align the (short) ends and hold them flat between your index finger and thumb. Use your free hand to get them in order. Once they're in order, keep holding them still between your index finger and thumb using one hand, then use your free hand to slot on the connector
Edit: also bending them back and forth a bit will soften them up and reduce them curling in all sorts of directions. It also weakens them, so don't overdo it (mostly only works for solid cable, the type meant for permanent installations like inside walls)